Hydrochloric Acid → HCID 23044277, compound

Participants

Reaction Steps

Sodium cyanoborohydride (0.69 g, 11 mmole) and 26 g of 30A molecular sieves were slowly added at room temperature to a stirred solution of 1-phenylmethyl-3-methyl-5-methoxycarbonyl-4-piperidone (5.04 g, 18.3 mmole) from Example 3 in 200 ml of methanol, 10.22 g (110 mmole) of aniline and 9.48 ml of 3.86N hydrochloric acid (36.6 mmole) in methanol. The reaction mixture was stirred at room temperature for 3 days, after which time the molecular sieves were filtered off and the solution was made acidic with 10 ml of 20% hydrochloric acid. The methanol was evaporated under vacuum and the residue was diluted with 100 ml of water then extracted with ether. The aqueous layer was then made alkaline with dilute aqueous sodium hydroxide and extracted with 3×100 ml of ether. The combined organic layers were concentrated under vacuum to yield 3.87 g (60%) of crude 1-phenylmethyl-3-methyl-5-methoxycarbonyl-4 -(N-phenylamino)piperidine.

Provenance & Evidence