(2S)-N2-(1-benzhydryl-3-azetanyl)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide → (2S)-1-(1,3-benzoxazol-2-yl)-N2-(1-ethyl-3-azetanyl)-2-piperidinecarboxamide

Participants

Reaction Steps

20% w/w Palladium hydroxide on carbon (31 mg) was added to a solution of (2S)-N2-(1-benzhydryl-3-azetanyl)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide (120 mg) [see Example 28] in ethanol (5 ml). The reaction mixture was hydrogenated for 18 hours at 414 kPa (60 p.s.i.), after which time additional 20% w/w palladium hydroxide on carbon (32 mg) was added and the mixture hydrogenated for a further 72 hours. The catalyst was then filtered off and washed with ethanol and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 90:10, by volume, dichloromethane:methanol in 2% increments, to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-(1-ethyl-3-azetanyl)-2-piperidinecarboxamide (37.1 mg) as a foam.

Provenance & Evidence