N,N-diethylheptan-1-amine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Mix 5.40 g (0.016 mole) of (Z)-4-(4-chlorophenyl)but-2-en-1-ol 4-methylbenzenesulfonate and 10.96 g (0.064 mole) of N,N-diethylheptanamine in 200 ml of acetonitrile. Stir the mixture at room temperature for 2 hours. Evaporate and recrystallize from ethyl acetate to yield the title compound, m.p. 79°-80° C. Evaporate recrystallize from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Mix 5.40 g (0.016 mole) of (Z)-4-(4-chlorophenyl)but-2-en-1-ol 4-methylbenzenesulfonate and 10.96 g (0.064 mole) of N,N-diethylheptanamine in 200 ml of acetonitrile. Stir the mixture at room temperature for 2 hours. Evaporate and recrystallize from ethyl acetate to yield the title compound, m.p. 79°-80° C. Evaporate recrystallize from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Heat a mixture of 6.0 g (0.03 mole) of 1-chloro-3-(4-chloro-2-butenyl)benzene and 3-chloro-4-(3-chlorophenyl)-1-butene (in a ratio of 4:3) and 5.1 g (0.03 mole) N,N-diethylheptanamine at 100° C. for about 20 hours. Dissolve in 100 ml water and wash with 3×75 ml hexane and then extract with methylene chloride. Dry methylene chloride extract over magnesium sulfate, filter and evaporate the solvent in vacuo to provide the title compound. Heat wash with 3×75 ml hexane extract with methylene chloride Dry methylene chloride extract over magnesium sulfate filter evaporate the solvent in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolve 35.55 g (0.1768 mole) of a mixture of 1-chloro-4-(4-chloro-2-butenyl)benzene and 1-chloro-4-(2-chloro-3-butenyl)benzene and 27.7 g (0.1607 mole) of N,N-diethyl-1-heptanamine in 220 ml of acetonitrile. Heat the reaction mixture to reflux for 6 hours. Follow the progress of the reaction by thin layer chromatography (acetonitrile: ammonium hydroxide, 95:5). At the completion of the reaction, evaporate solvent and dissolve the residue in 400 ml distilled water. Add solid sodium bicarbonate until pH of solution is 8.5. Wash the aqueous mixture with 4×200 ml petroleum ether and then 5×200 ml Et2O. Add 1N HCl to aqueous layer until pH=1 and then extract with 3×200 ml methylene chloride. Dry over magnesium sulfate, filter and evaporate solvent. Dissolve the material in 150 ml of 2-butanone and then add diethyl ether until solution becomes cloudy. Warm solution until clear and then cool and store in freezer for 3 hours to complete crystallization and then filter title compound. Recrystallize a second time (2-butanone/ether) to provide the title compound in 60% yield. Heat the reaction mixture to reflux for 6 hours At the completion of the reaction evaporate solvent dissolve the residue in 400 ml distilled water Add solid sodium bicarbonate until pH of solution Wash the aqueous mixture with 4×200 ml petroleum ether Add 1N HCl to aqueous layer until pH=1 extract with 3×200 ml methylene chloride Dry over magnesium sulfate filter evaporate solvent Dissolve the material in 150 ml of 2-butanone Warm solution until clear and then cool crystallization filter title compound Recrystallize a second time (2-butanone/ether)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolve 35.55 g (0.1768 mole) of a mixture of 1-chloro-4-(4-chloro-2-butenyl)benzene and 1-chloro-4-(2-chloro-3-butenyl)benzene and 27.7 g (0.1607 mole) of N,N-diethyl-1-heptanamine in 220 ml of acetonitrile. Heat the reaction mixture to reflux for 6 hours. Follow the progress of the reaction by thin layer chromatography (acetonitrile: ammonium hydroxide, 95:5). At the completion of the reaction, evaporate solvent and dissolve the residue in 400 ml distilled water. Add solid sodium bicarbonate until pH of solution is 8.5. Wash the aqueous mixture with 4×200 ml petroleum ether and then 5×200 ml Et2O. Add 1N HCl to aqueous layer until pH=1 and then extract with 3×200 ml methylene chloride. Dry over magnesium sulfate, filter and evaporate solvent. Dissolve the material in 150 ml of 2-butanone and then add diethyl ether until solution becomes cloudy. Warm solution until clear and then cool and store in freezer for 3 hours to complete crystallization and then filter title compound. Recrystallize a second time (2-butanone/ether) to provide the title compound in 60% yield. Heat the reaction mixture to reflux for 6 hours At the completion of the reaction evaporate solvent dissolve the residue in 400 ml distilled water Add solid sodium bicarbonate until pH of solution Wash the aqueous mixture with 4×200 ml petroleum ether Add 1N HCl to aqueous layer until pH=1 extract with 3×200 ml methylene chloride Dry over magnesium sulfate filter evaporate solvent Dissolve the material in 150 ml of 2-butanone Warm solution until clear and then cool crystallization filter title compound Recrystallize a second time (2-butanone/ether)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Combine 1.00 g (4.76 mmole) 1-chloro-2-(4-chloro-2- butenyl)benzene and 1.77 g (4.76 mmole) N,N-diethylheptanamine and heat at 100° C. ca. 20 hrs. Follow the progress of the reaction by TLC on silica gel (acetonitrile: ammonium hydroxide, 9:1). At the completion of the reaction, decant off the top layer of the two phase reaction mixture. Dissolve the bottom layer in 50 ml H2O. Extract with 3×100 ml hexane, 1×25 ml CH2Cl2. Dry CH2Cl2 over MgSO4 and treat with activated charcoal. Evaporate the solvents to provide the title compound. the progress of the reaction by TLC on silica gel (acetonitrile: ammonium hydroxide, 9:1) At the completion of the reaction decant off the top layer of the two phase reaction mixture Extract with 3×100 ml hexane, 1×25 ml CH2Cl2 Dry CH2Cl2 over MgSO4 and treat with activated charcoal Evaporate the solvents

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolve 50.90 ml (0.5 moles) diethylamine and 57.10 g (0.5 mole) heptaldehyde in 500 ml methanol and stir at room temperature for one hour. Slowly add 31.42 g sodium cyanoborohydride in 500 ml methanol to the stirred reaction mixture. Add glacial acetic acid to the reaction mixture until pH=6. Stir at room temperature overnight. Concentrate reaction mixture volume to 300 ml and then add 500 ml distilled water. Add concentrated hydrochloric acid until pH=1. Extract with 5×250 ml methylene chloride. Evaporate organic solvent and then dissolve the residue in 400 ml 0.1N HCl. Wash aqueous solution with 3×200 ml diethyl ether and then add 2N NaOH until solution is basic (pH=12). Extract with 3×200 ml diethyl ether. Dry over MgSO4, filter and evaporate, the distill in vacuo to obtain 46.0 g (53.7%) title compound. Stir at room temperature overnight Concentrate reaction mixture volume to 300 ml add 500 ml distilled water Add concentrated hydrochloric acid until pH=1 Extract with 5×250 ml methylene chloride Evaporate organic solvent and then dissolve the residue in 400 ml 0.1N HCl Wash aqueous solution with 3×200 ml diethyl ether and then add 2N NaOH until solution Extract with 3×200 ml diethyl ether Dry over MgSO4 filter evaporate the distill in vacuo

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Mix 5.40 g (0.016 mole) of (Z)-4-(4-chlorophenyl)but-2-en-1-ol 4-methylbenzenesulfonate and 10.96 g (0.064 mole) of N,N-diethylheptanamine in 200 ml of acetonitrile. Stir the mixture at room temperature for 2 hours. Evaporate and recrystallize from ethyl acetate to yield the title compound, m.p. 79°-80° C. Evaporate recrystallize from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Heat a mixture of 6.0 g (0.03 mole) of 1-chloro-3-(4-chloro-2-butenyl)benzene and 3-chloro-4-(3-chlorophenyl)-1-butene (in a ratio of 4:3) and 5.1 g (0.03 mole) N,N-diethylheptanamine at 100° C. for about 20 hours. Dissolve in 100 ml water and wash with 3×75 ml hexane and then extract with methylene chloride. Dry methylene chloride extract over magnesium sulfate, filter and evaporate the solvent in vacuo to provide the title compound. Heat wash with 3×75 ml hexane extract with methylene chloride Dry methylene chloride extract over magnesium sulfate filter evaporate the solvent in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolve 35.55 g (0.1768 mole) of a mixture of 1-chloro-4-(4-chloro-2-butenyl)benzene and 1-chloro-4-(2-chloro-3-butenyl)benzene and 27.7 g (0.1607 mole) of N,N-diethyl-1-heptanamine in 220 ml of acetonitrile. Heat the reaction mixture to reflux for 6 hours. Follow the progress of the reaction by thin layer chromatography (acetonitrile: ammonium hydroxide, 95:5). At the completion of the reaction, evaporate solvent and dissolve the residue in 400 ml distilled water. Add solid sodium bicarbonate until pH of solution is 8.5. Wash the aqueous mixture with 4×200 ml petroleum ether and then 5×200 ml Et2O. Add 1N HCl to aqueous layer until pH=1 and then extract with 3×200 ml methylene chloride. Dry over magnesium sulfate, filter and evaporate solvent. Dissolve the material in 150 ml of 2-butanone and then add diethyl ether until solution becomes cloudy. Warm solution until clear and then cool and store in freezer for 3 hours to complete crystallization and then filter title compound. Recrystallize a second time (2-butanone/ether) to provide the title compound in 60% yield. Heat the reaction mixture to reflux for 6 hours At the completion of the reaction evaporate solvent dissolve the residue in 400 ml distilled water Add solid sodium bicarbonate until pH of solution Wash the aqueous mixture with 4×200 ml petroleum ether Add 1N HCl to aqueous layer until pH=1 extract with 3×200 ml methylene chloride Dry over magnesium sulfate filter evaporate solvent Dissolve the material in 150 ml of 2-butanone Warm solution until clear and then cool crystallization filter title compound Recrystallize a second time (2-butanone/ether)