1-[2-AMino-1-(4-Methoxyphenyl)ethyl]cyclohexanol

Synthesis

To a mechanically stirred solution of AlCl3 (103.60 g, 0.779 mol) in THF (900 ml), at 0 ºC, LiAlH4 (59.80 g, 1.575 mol) was added cautiously, in portions. Temperature was maintained below 10 ºC. A solution of 2-(1-Hydroxycyclohexyl)-2-(4-methoxyphenyl) acetonitrile(130.0 g, 0.530 mol) in THF (500 ml) was added drop-wise over a period of 1.5 hours. The reaction mixture was then brought to room temperature and stirred for 30 minutes. The reaction mixture was again cooled in an ice-salt bath. The reaction was quenched with ethyl acetate (60 ml) maintaining the temperature below 10 ºC. The reaction mixture was then transferred to a beaker, cooled externally in an ice-salt bath and treated very cautiously with 25% aq. NaOH solution (360 ml) with mechanical stirring. (After addition of about 50 ml 25% aq. NaOH solution, a hard solid was formed, cooling was removed and the contents were stirred manually during the addition of remaining NaOH solution). The solid was loosened at room temperature, which was further stirred for 1 hour. A bright white solid appeared. The solid was filtered off, washed thoroughly with ethyl acetate. The filtrate was concentrated in vacuo and combined with the above washings, washed with brine, dried over anhydrous Na2SO4, filtered and ethyl acetate removed under reduced pressure to obtain aminoalcohol 38 as a thick yellow oil (129.4 g).

Chemical Properties

Pale Yellow Oil

Uses

An intermediate in the synthesis of N,O-Didesmethylvenlafaxine, a metabolite of Venlafaxine

Definition

ChEBI: A monomethoxybenzene that is the N,N-didesmethyl derivative of venlafaxine.