2-phenylmethoxypropan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (300 mg, 1.125 mmol) in toluene (10 mL), triphosgene (126 mg, 0.45 mmol) and triethylamine (0.195 mL, 1.35 mmol) were added. The reaction mixture was stirred at 80° C. for 3 hours. Then it was cooled to room temperature and all solvent was evaporated. The residue was dissolved in DMF (1 mL) and 2-benzyloxypropylamine (185.6 mg, 1.125 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours. Chromatography of the resulting liquid on silica gel (50% Ethyl acetate/Hexane) gave desired product (160 mg, 41%). EI-MS m/z 346.4 (M+). mp: 64.6-65.2° C. Then it was cooled to room temperature all solvent was evaporated The residue was dissolved in DMF (1 mL) The reaction mixture was stirred at 80° C. for 16 hours

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (300 mg, 1.125 mmol) in toluene (10 mL), triphosgene (126 mg, 0.45 mmol) and triethylamine (0.195 mL, 1.35 mmol) were added. The reaction mixture was stirred at 80° C. for 3 hours. Then it was cooled to room temperature and all solvent was evaporated. The residue was dissolved in DMF (1 mL) and 2-benzyloxypropylamine (185.6 mg, 1.125 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours. Chromatography of the resulting liquid on silica gel (50% Ethyl acetate/Hexane) gave desired product (160 mg, 41%). EI-MS m/z 346.4 (M+). mp: 64.6-65.2° C. Then it was cooled to room temperature all solvent was evaporated The residue was dissolved in DMF (1 mL) The reaction mixture was stirred at 80° C. for 16 hours

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (300 mg, 1.125 mmol) in toluene (10 mL), triphosgene (126 mg, 0.45 mmol) and triethylamine (0.195 mL, 1.35 mmol) were added. The reaction mixture was stirred at 80° C. for 3 hours. Then it was cooled to room temperature and all solvent was evaporated. The residue was dissolved in DMF (1 mL) and 2-benzyloxypropylamine (185.6 mg, 1.125 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours. Chromatography of the resulting liquid on silica gel (50% Ethyl acetate/Hexane) gave desired product (160 mg, 41%). EI-MS m/z 346.4 (M+). mp: 64.6-65.2° C. Then it was cooled to room temperature all solvent was evaporated The residue was dissolved in DMF (1 mL) The reaction mixture was stirred at 80° C. for 16 hours

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of styrene oxide (1.96 g, 0.010 mol) and 2-benzyloxypropylamine (2.48 g, 0.15 mol) was heated at 140° C. for 6 hours and then allowed to cool to ambient temperature and stand for 12 hours. The solidified reaction mixture was triturated with isooctane and filtered to obtain an impure solid that was recrystallized from isooctane to obtain 2.40 g of a white solid (84% yield); mp 90°-100° C. (undefined). to cool to ambient temperature The solidified reaction mixture was triturated with isooctane filtered to obtain an impure solid that was recrystallized from isooctane

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of trans-stilbene oxide (1.96 g, 0.010 mol) and 2-benzyloxypropylamine (2.48 g, 0.015 mol) was heated at 140° C. for 6 hours and then allowed to stand at ambient temperature for 12 hours. The solidified reaction mixture was triturated with petroleum ether and filtered to obtain 2.72 g of a solid. Mass spectral analysis showed starting materials present. Recrystallization from isooctane gave 2.16 g (60%) of the product as a white solid; mp 114°-119° C. The solidified reaction mixture was triturated with petroleum ether filtered

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (300 mg, 1.125 mmol) in toluene (10 mL), triphosgene (126 mg, 0.45 mmol) and triethylamine (0.195 mL, 1.35 mmol) were added. The reaction mixture was stirred at 80° C. for 3 hours. Then it was cooled to room temperature and all solvent was evaporated. The residue was dissolved in DMF (1 mL) and 2-benzyloxypropylamine (185.6 mg, 1.125 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours. Chromatography of the resulting liquid on silica gel (50% Ethyl acetate/Hexane) gave desired product (160 mg, 41%). EI-MS m/z 346.4 (M+). mp: 64.6-65.2° C. Then it was cooled to room temperature all solvent was evaporated The residue was dissolved in DMF (1 mL) The reaction mixture was stirred at 80° C. for 16 hours