Ammonia → (S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine

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Reaction Steps

Pure (S)—N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine dibenzoyl-L-tartaric acid salt (8a) (100 gm) obtained in example 8 was stirred in a mixture of water (500 ml) and cyclohexane (250 ml). Aqueous ammonia solution (100 ml) was charged to adjust the pH of slurry to 10.8 and the biphasic mass was stirred for 15-30 minutes. The organic layer was separated and aqueous layer was extracted with cyclohexane (250 ml). Organic layers were combined, washed with water and concentrated to get thick oily mass (S)—N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine (6a). Yield: 45.0 gm. The oily mass obtained above was dissolved in toluene (225 ml) and diisopropylethylamine (23.18 gm) was added followed by phenyl chloroformate (35.10 gm) in drop wise manner. The solution was warmed to 55° C. and stirred for 2 hours. The reaction mass was cooled down, basified with 2% NaHCO3 solution (225 ml) and organic layer was separated. Organic layer was washed with water and concentrated under reduced pressure to get oily mass of carbamate intermediate (10).

Provenance & Evidence