N-butyl-N-(3-chloropropyl)butan-1-amine;hydrochloride

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 9.69 g of dibutylamino propylchloride HCl salt (IV) (0.04 mol, 1 eq), 5 g of 4-hydroxybenzaldehyde (III) (0.04 mol, 1 eq), 17 g of potassium carbonate (0.12 mol, 3 eq) and 30 mL of MEK are added to the reaction flask. The suspension is heated to 80° C. and it is stirred for 10 hours at this temperature. Then the mixture is cooled to room temperature, 40 mL of water is added and the brown solution is stirred for 30 min. After phase separation the organic phase is washed with 15 mL of water and the solvent is evaporated to obtain 10.6 g of compound (V) as a yellowish-brown solid (89%). Then the mixture is cooled to room temperature the brown solution is stirred for 30 min After phase separation the organic phase is washed with 15 mL of water the solvent is evaporated

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

実験手順: 18.6 g of 68.4% 1-chloro-3-(di-n-butylamino)-propane hydrochloride (52.6 mmol) are placed in an equipped reactor and then 9.97 g of a 20% aqueous ammonia solution (56.9 mmol) are added at 20° C. The mixture is stirred for 15 minutes, and then the phases are decanted off and separated: the bottom phase consists of 1-chloro-3-(di-n-butylamino)-propane in the form of a free base. This phase is washed with 10 ml of water and 9.99 g of 1-chloro-3-(di-n-butylamino)-propane are thus isolated. the phases are decanted off separated This phase is washed with 10 ml of water and 9.99 g of 1-chloro-3-(di-n-butylamino)-propane are thus isolated

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

実験手順: Into a 1 l reactor, there are introduced 288.4 g (3.392 mol) of 20% aqueous ammonia, and then there are added, over 10 minutes and at room temperature (22±2° C.), 618 g (1.696 mol) of 1-dibutylamino-3-chloropropane hydrochloride (titer 66.5%). The medium is stirred for 45 minutes at room temperature and it is allowed to separate by settling for 30 minutes. The bottom aqueous phase (pH=11) is removed, and the organic phase is washed with 300 ml of deionized water at room temperature. The medium is stirred for 30 minutes, separated by settling for 30 minutes and the bottom aqueous phase (pH=9) is drawn off. to separate by settling for 30 minutes The bottom aqueous phase (pH=11) is removed the organic phase is washed with 300 ml of deionized water at room temperature The medium is stirred for 30 minutes separated by settling for 30 minutes

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

実験手順: The process is performed in the same manner as previously (Example 13), starting with 138 g (1.466 mol; 1.15 eq.) of phenol, 109.5 g (2.738 mol; 2.15 eq.) of NaOH, 530 ml of distilled water and 308.9 g (1.275 mol; 1 eq.) of N-(3-chloropropyl)-N,N-dibutylamine hydrochloride. The mixture is refluxed for 16 hours. The oil formed is separated out by settling and washed with 500 ml of water and then diluted with 500 ml of MTBE and washed with 500 ml of 2% HCl. The MTBE phase is concentrated under vacuum and the oil is dried by azeotropic distillation with DCM. 307.1 g of the crude derivative N,N-dibutyl-N-(3-phenoxypropyl)amine are obtained. The mixture is refluxed for 16 hours The oil formed is separated out washed with 500 ml of water diluted with 500 ml of MTBE washed with 500 ml of 2% HCl The MTBE phase is concentrated under vacuum the oil is dried by azeotropic distillation with DCM

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

実験手順: 288.4 g (3.392 mol) of 20% aqueous ammonia are introduced into a 1 l reactor and then 618 g (1.696 mol) of 1-dibutylamino-3-chloropropane hydrochloride (assay 66.5%) are added over 10 minutes and at ambient temperature (22±2° C.). The mixture is stirred for 45 minutes at ambient temperature and is left to separate by settling for 30 minutes. The lower aqueous phase (pH=11) is removed and the organic phase is washed with 300 ml of deionized water at ambient temperature. Stirring is carried out for 30 minutes, separation by settling is carried out for 30 minutes and the lower aqueous phase (pH=9) is removed. is left to separate by settling for 30 minutes The lower aqueous phase (pH=11) is removed the organic phase is washed with 300 ml of deionized water at ambient temperature Stirring is carried out for 30 minutes separation by settling is carried out for 30 minutes the lower aqueous phase (pH=9) is removed

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 9.69 g of dibutylamino propylchloride HCl salt (IV) (0.04 mol, 1 eq), 5 g of 4-hydroxybenzaldehyde (III) (0.04 mol, 1 eq), 17 g of potassium carbonate (0.12 mol, 3 eq) and 30 mL of MEK are added to the reaction flask. The suspension is heated to 80° C. and it is stirred for 10 hours at this temperature. Then the mixture is cooled to room temperature, 40 mL of water is added and the brown solution is stirred for 30 min. After phase separation the organic phase is washed with 15 mL of water and the solvent is evaporated to obtain 10.6 g of compound (V) as a yellowish-brown solid (89%). Then the mixture is cooled to room temperature the brown solution is stirred for 30 min After phase separation the organic phase is washed with 15 mL of water the solvent is evaporated

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

実験手順: 18.6 g of 68.4% 1-chloro-3-(di-n-butylamino)-propane hydrochloride (52.6 mmol) are placed in an equipped reactor and then 9.97 g of a 20% aqueous ammonia solution (56.9 mmol) are added at 20° C. The mixture is stirred for 15 minutes, and then the phases are decanted off and separated: the bottom phase consists of 1-chloro-3-(di-n-butylamino)-propane in the form of a free base. This phase is washed with 10 ml of water and 9.99 g of 1-chloro-3-(di-n-butylamino)-propane are thus isolated. the phases are decanted off separated This phase is washed with 10 ml of water and 9.99 g of 1-chloro-3-(di-n-butylamino)-propane are thus isolated