Ammonia → HCID 86759288, compound

Participants

Reaction Steps

A suspension containing 9.1 g (0.02 mol) of (±)-trans-1-benzyl-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine hydrochloride in the mixture of 100 ml of chloroform and 50 ml of water is alkalinized to pH 9 by adding concentrated aqueous ammonia solution. After separation of the phases, the aqueous layer is extracted with 20 ml of chloroform. The combined organic phase is dried over magnesium sulfate and, after filtering the drying agent the solution is evaporated to solvent-free. The evaporation residue is dissolved in 120 ml of ethanol and hydrogenated in an autoclave in the presence of 0.8 g of 10% palladium-on-carbon catalyst at 40° C., under 5×105 Pa pressure for 2 to 3 hours. After taking up the hydrogen, the catalyst is filtered and the filtrate is evaporated to solvent-free. The evaporation residue (weighing 6.6 g) is dissolved in 80 ml of methanol, a solution of 3 g (0.02 mol) of (+)-D-tartaric acid in 20 ml of methanol is added at room temperature and the mixture is stirred for 5 hours. The precipitated crystalline product is filtered to yield 3.2 g (66%) of (−)-trans-4-(4-flurophenyl)-3-(3,4-metylenedioxyphenoxymethyl)piperidine (+)-D-tartarate, m.p.: 178-180° C.; [α]D20−50.5° (c=1, dimethylformamide).

Provenance & Evidence