1-(4-bromophenyl)propan-2-amine

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

実験手順: 17.0 mL (179.7 mmol) acetic anhydride are added to a mixture of 24.2 g (113 mmol) 1-(4-bromophenyl)propane-2-amine and 20 mL AcOH and the reaction mixture is stirred at r.t. over night. The solvent is evaporated in vacuo, and the residue partitonated between TBME and a saturated aq. NaHCO3 solution. The layers are separated and the organic layer is washed with water, dried with Na2SO4, filtered and the solvent is removed in vacuo. The crude product is triturated with DIPE. The solvent is evaporated in vacuo The layers are separated the organic layer is washed with water dried with Na2SO4 filtered the solvent is removed in vacuo The crude product is triturated with DIPE

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

実験手順: A mixture of 25.0 g (0.12 mol) 4-bromophenylacetone and 400 mL 7N ammonia in MeOH is charged with 1.20 g Raney nickel. The mixture is stirred in an hydrogen atmosphere (15 psi) at r.t. over night. Again 0.6 g Raney nickel are added and the mixture is stirred again for 3.5 h. After complete reaction, the mixture is filtrated. The residue is washed with MeOH and the solvent of the filtrate is removed in vacuo. The crude product is used without further purification. After complete reaction the mixture is filtrated The residue is washed with MeOH the solvent of the filtrate is removed in vacuo The crude product is used without further purification

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

実験手順: A mixture of 25.0 g (0.12 mol) 4-bromophenylacetone and 400 mL 7N ammonia in MeOH is charged with 1.20 g Raney nickel. The mixture is stirred in an hydrogen atmosphere (15 psi) at r.t. over night. Again 0.6 g Raney nickel are added and the mixture is stirred again for 3.5 h. After complete reaction, the mixture is filtrated. The residue is washed with MeOH and the solvent of the filtrate is removed in vacuo. The crude product is used without further purification. After complete reaction the mixture is filtrated The residue is washed with MeOH the solvent of the filtrate is removed in vacuo The crude product is used without further purification

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

実験手順: To a solution of 1-(4-bromophenyl)propan-2-amine (0.5 g, 2 mmol) in methylene chloride (5 mL) was added pyridine (380 uL, 4.7 mmol) and methyl chloroformate (270 uL, 3.5 mmol, Aldrich, Cat. No. M35304). The reaction mixture was stirred at r.t. overnight, and concentrated under reduced pressure. The residue was dissolved in EtOAc, and washed with NaHCO3 aqueous solution, 1N HCl aqueous solution and brine. The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatograph on a silica gel column using 25% Ethyl acetate in hexane to afford the desired compound. LCMS (M+H)+: m/z=272.2. concentrated under reduced pressure The residue was dissolved in EtOAc washed with NaHCO3 aqueous solution, 1N HCl aqueous solution and brine The organic layer was dried with MgSO4 filtered concentrated under reduced pressure The residue was purified by flash chromatograph on a silica gel column

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

実験手順: To a mixture of 2.0 M of ammonia in ethanol (117 mL, 235 mmol, Aldrich, Cat. No. 392685) and titanium tetraisopropoxide (27.7 mL, 93.9 mmol, Aldrich, Cat. No. 377996) was added 1-(4-bromophenyl)acetone (10.0 g, 46.9 mmol, Alfa Aesar, Cat. No. A19028). The reaction mixture was stirred at r.t. under nitrogen overnight. Sodium tetrahydroborate (2.66 g, 70.4 mmol) was added. The mixture was stirred at r.t. for additional 3 h. The reaction mixture was quenched with 2M ammonia in water, and filtered. The solid was washed with AcOEt. The filtrate was concentrated to remove most ethanol, and then was washed with AcOEt twice. The combined organic layers were extracted with 1N HCl aqueous solution (twice). The aqueous HCl solutions were combined, and adjusted with ammonia aqueous solution to pH=10. The result solution was extracted with CH2Cl2. The organic layer was dried with MgSO4, filtered, and concentrated to afford the desired compound which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=214.2. The mixture was stirred at r.t. for additional 3 h The reaction mixture was quenched with 2M ammonia in water filtered The solid was washed with AcOEt The filtrate was concentrated to remove most ethanol was washed with AcOEt twice The combined organic layers were extracted with 1N HCl aqueous solution (twice) The result solution was extracted with CH2Cl2 The organic layer was dried with MgSO4 filtered concentrated

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

実験手順: A mixture of 25.0 g (0.12 mol) 4-bromophenylacetone and 400 mL 7N ammonia in MeOH is charged with 1.20 g Raney nickel. The mixture is stirred in an hydrogen atmosphere (15 psi) at r.t. over night. Again 0.6 g Raney nickel are added and the mixture is stirred again for 3.5 h. After complete reaction, the mixture is filtrated. The residue is washed with MeOH and the solvent of the filtrate is removed in vacuo. The crude product is used without further purification. After complete reaction the mixture is filtrated The residue is washed with MeOH the solvent of the filtrate is removed in vacuo The crude product is used without further purification

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

実験手順: 17.0 mL (179.7 mmol) acetic anhydride are added to a mixture of 24.2 g (113 mmol) 1-(4-bromophenyl)propane-2-amine and 20 mL AcOH and the reaction mixture is stirred at r.t. over night. The solvent is evaporated in vacuo, and the residue partitonated between TBME and a saturated aq. NaHCO3 solution. The layers are separated and the organic layer is washed with water, dried with Na2SO4, filtered and the solvent is removed in vacuo. The crude product is triturated with DIPE. The solvent is evaporated in vacuo The layers are separated the organic layer is washed with water dried with Na2SO4 filtered the solvent is removed in vacuo The crude product is triturated with DIPE

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

実験手順: A mixture of 25.0 g (0.12 mol) 4-bromophenylacetone and 400 mL 7N ammonia in MeOH is charged with 1.20 g Raney nickel. The mixture is stirred in an hydrogen atmosphere (15 psi) at r.t. over night. Again 0.6 g Raney nickel are added and the mixture is stirred again for 3.5 h. After complete reaction, the mixture is filtrated. The residue is washed with MeOH and the solvent of the filtrate is removed in vacuo. The crude product is used without further purification. After complete reaction the mixture is filtrated The residue is washed with MeOH the solvent of the filtrate is removed in vacuo The crude product is used without further purification