Dibah → HCID 86753143, compound

Participants

Reaction Steps

Starting from (RS)-2-dimethylaminomethyl-cyclohexanone and 1-bromo-2-methoxy-benzene, (1RS,2RS)-2-dimethylaminomethyl-1-(2-methoxy-phenyl)-cyclohexanol hydrochloride (30) was obtained, under the conditions given in Example 1 (1st step) and using ether as a solvent, in a yield of 47%. The base was released from (30) with dichloromethane/sodium hydroxide solution. After drying the solution, the dichloromethane was distilled off under vacuum. 30.0 g (0.1 mole) of the base were reacted with diisobutylaluminium as in Example 2. 22.7 g (78% theoretical) (1RS,2RS)-2-(2-dimethylaminomethyl-1-hydroxy-cyclo-hexyl-phenol hydrochloride (31) were obtained, with a melting point of 168°-170° C. 28.6 g (0.1 mole) of compound (31) were reacted with 450 ml of concentrated formic acid as in Example 5. The crude base obtained was introduced on to a column packed with silica gel and eluted with 7:1 diisopropyl ether/methanol. 21 g base were obtained, from which 18.6 g (69% theoretical) of hydrochloride (29), which had a melting point of 168° C., was obtained with concentrated hydrochloric acid in acetone.

Provenance & Evidence