Ammonia → N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine

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Reaction Steps

(R,S)—N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine oxalate salt (5, HA=oxalic acid) (255 gm) was suspended in a mixture of water (1275 ml) and cyclohexane (765 ml). This suspension was basified with aqueous ammonia solution (pH 12.5-13.5). Organic layer was separated, washed with water and concentrated under reduced pressure to give oily mass of racemic condensed compound, (R,S)—N.N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine (6a+6b) (195 gm). The oily mass was dissolved in 2000 ml of mixture of methanol (5%) and ethyl acetate (95%). To this clear solution 1.0 mole equivalent of di-benzoyl-(L)-tartaric acid monohydrate (236.4 gm) was added. The clear solution was stirred for half an hour and seeded with crystals of (S)—N,N-dimethyl-3-(1-naphthylenyloxy)-3-(2-thienyl)propanamine dibenzoyl-(L)-tartarate salt (8a). The solution was stirred for 12-15 hours at 25-30° C. to get white thick slurry. The solid obtained was filtered, washed with ethanol (255 ml) and dried under reduced pressure.

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