1-(benzylamino)-3-chloropropan-2-ol

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

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

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

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

Procedure: 333 g of N-benzyl-3-amino-1-chloropropan-2-ol was taken up in 1665 ml of triethylamine and 10 g of tetrabutylammonium iodide was added. The resulting mixture was stirred under reflux for 13 hours, after which it was cooled, the hydrochloride precipitate filtered off and the filtrate washed twice with triethylamine. The combined filtrates were evaporated to yield 252 g of an oil, which was crystallized from 250 ml of toluene and 50 ml of hexane to yield 180.8 g of l as white crystals, m.p.: 66°-67° C., being a yield (based on amino-propanol) of 66.5% . under reflux for 13 hours after which it was cooled the hydrochloride precipitate filtered off the filtrate washed twice with triethylamine The combined filtrates were evaporated

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

Procedure: 10 g of 1A was heated under reflux in 150 ml of water with stirring for 24 hours. The reaction mixture was cooled, the aqueous solution was decanted from insoluble material and made alkaline by the addition of solid sodium hydroxide. The oil which separated was extracted with dichloromethane and the extracts were washed with water and dried. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel using acetone as eluent, followed by recrystallization from toluene to give 1, as a crystalline solid, m.p.: 64.5°-65.5° C., in 27% yield. The reaction mixture was cooled the aqueous solution was decanted from insoluble material by the addition of solid sodium hydroxide The oil which separated was extracted with dichloromethane the extracts were washed with water dried The solvent was removed under reduced pressure the residue was purified by chromatography on silica gel followed by recrystallization from toluene to give 1

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

Procedure: 10 g of 1A was heated under reflux in 150 ml of water with stirring for 24 hours. The reaction mixture was cooled, the aqueous solution was decanted from insoluble material and made alkaline by the addition of solid sodium hydroxide. The oil which separated was extracted with dichloromethane and the extracts were washed with water and dried. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel using acetone as eluent, followed by recrystallization from toluene to give 1, as a crystalline solid, m.p.: 64.5°-65.5° C., in 27% yield. The reaction mixture was cooled the aqueous solution was decanted from insoluble material by the addition of solid sodium hydroxide The oil which separated was extracted with dichloromethane the extracts were washed with water dried The solvent was removed under reduced pressure the residue was purified by chromatography on silica gel followed by recrystallization from toluene to give 1

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

Procedure: 46.25 g of epichlorohydrin, 33.5 g of benzylamine and 250 ml of cyclohexane were stirred together at ambient temperature for 24 hours. The precipitate formed was filtered off and recrystallized from toluene to give N-benzyl-3-amino-1-chloropropan-2-ol (1A), as a crystalline solid, m.p.: 70°-71° C., in 55% yield. The precipitate formed was filtered off recrystallized from toluene

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

Procedure: reacting epichlorohydrin with benzylamine to form the addition product, N-benzyl-3-amino-1-chloropropan-2ol (I);

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

Procedure: reacting epichlorohydrin with benzylamine to form the addition product, N-benzyl-3-amino-1-chloropropan-2ol (I);

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

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

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