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

Participants

Reaction Conditions

Reaction Steps

N,N-dimethyl-3-(2-thienyl)-3-hydroxypropanamine (2, racemic hydroxy compound) (50 gm) was dissolved in dimethyl sulfoxide (250 ml). To the clear solution sodamide (13.7 gm) was added at 20-25° C. in small lots within 10-15 minutes under nitrogen atmosphere. The resulting reaction mass was stirred for half an hour to get a clear solution. To this solution 1-fluoronaphthalene (3) (43.4 gm) was added in 20-25 minutes. The temperature was raised to 80-95° C. and stirred for 3-5 hours, then cooled to 25-30° C. Reaction mass added into cold-water (500 ml), pH was adjusted to 5.5-6.0 with acetic acid. Aqueous reaction mass washed with cyclohexane followed by pH adjustment between 10.5-11.0 with caustic solution. Reaction mixture was extracted with cyclohexane and organic layer concentrated under reduced pressure to provide thick oily mass of (±)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine (4). The oily mass was dissolved in ethyl acetate (250 ml) and oxalic acid (30 gm) was added. Stirred at 50-60° C. for 1 hour then at 25-30° C. for 2 hours. Solid was filtered and dried to give racemic N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine oxalate (5, HA=oxalic acid) as white solid. Yield: 75 gm.

Provenance & Evidence