Thiophene → (+/-)-cis-4-[4-(5,6-dihydro-11H-imidazo [2,1-b][3]benzazepin-11-ylidene)-1-piperidinyl]-1-(3,5-dimethylbenzoyl)-2-(phenylmethyl)piperidine

Participants

Reaction Steps

A mixture of (±)-1-(3,5-dimethylbenzoyl)-2-(phenylmethyl)-4-piperidinone (2.5 g) and 6,11-dihydro-11-(4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepine (2.1 g) in methanol (150 ml) and a solution of thiophene (4%; 1 ml) was hydrogenated at 50° C. overnight with palladium on activated carbon (10%; 2 g) as a catalyst. After uptake of hydrogen, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/ (CH3OH/ NH3) 98/2 to 95/5). The desired fraction was collected, the solvent evaporated, yielding 0.54 g (12.3%) of (±)-cis-4-[4-(5,6-dihydro-11H-imidazo [2,1-b][3]benzazepin-11-ylidene)-1-piperidinyl]-1-(3,5-dimethylbenzoyl)-2-(phenylmethyl)piperidine (comp. 1; mp. 138.7° C.).

Provenance & Evidence