1,2-Dichloroethane → HCID 69337727, compound

Participants

Reaction Steps

Benzo[b]thiophen-3-yl-ethylamine (289 mg, 1.6 mmol) was dissolved in dry 1,2-dichloroethane (10 ml) under argon and, after addition of 4-dimethylamino-4-phenylcyclohexanone (354 mg, 1.6 mmol) and sodium sulfate (2 g), the mixture was stirred for one hour at RT. Sodium triacetoxyborohydride (440 mg, 2.0 mmol) was then added to the reaction mixture in one portion. After 3 days, glacial acetic acid (4 mmol) was subsequently added and the mixture was stirred for a further 24 hours at RT. For working up, water (20 ml) was added and the reaction mixture was filtered with suction. The solid obtained was dissolved with two molar sodium carbonate solution and ethyl acetate. The organic phase was separated off, dried over sodium sulfate and filtered and the filtrate concentrated. The solid but tacky residue obtained (213 mg) was dissolved in 2-butanone (5 ml), and ethanolic HCl (500 μl, 1.5 mmol) was added at RT. After two hours, the solution was concentrated to dryness and the residue was suspended in diethyl ether (5 ml), filtered off with suction and rinsed with diethyl ether (3×3 ml). A mixture of cis- and trans-N′-(2-benzo[b]thiophen-3-yl-ethyl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine dihydrochloride (217 mg, m.p. 164-167° C.) was obtained as a beige-brown solid.

Provenance & Evidence