Dimethylamine → 1-(Dimethylamino)-3-(4-nitrophenoxy)propan-2-ol

Participants

Reaction Steps

To a solution of 2-(4-nitrophenoxymethyl)-oxirane (0.1 mol, 19.52 g) in methanol (150 mL) and dimethyl formamide (50 mL) was added a 2 M solution of dimethylamine in methanol (0.2 mol, 100 mL), and the mixture was stirred at rt overnight. The solvent was evaporated, and the residue was dissolved in a mixture of methylene chloride (300 mL) and methanol (30 mL). A portion of 1 N HCl in diethyl ether (150 mL) was added dropwise, and an oil formed. The oil was separated (ethereal layer was decanted), and the oil was dried under vacuum, yielding 1-dimethylamino-3-(4-nitro-phenoxy)-propan-2-ol (16.6 g) as its hydrochloride salt. MS (ES+) m/z: 240.9 (M+H+). The compound was used as such for the next reaction.

Provenance & Evidence