O-ethyl 1-(phenylmethyl)-4-piperidineethanimidate hydrochloride → HCID 14012850, compound
Reaction equation
Cl.[C:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16](=[NH:20])OCC)[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][NH:29][C:30]2[C:31](N)=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:24][CH:23]=1>CO>[CH3:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][N:29]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=3[N:20]=[C:16]2[CH2:15][CH:12]2[CH2:11][CH2:10][N:9]([CH2:8][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:14][CH2:13]2)=[CH:26][CH:27]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 116.5 parts of O-ethyl 1-(phenylmethyl)-4-piperidineethanimidate hydrochloride, 61.5 parts of N1 -[(4-methylphenyl)methyl]-1,2-benzenediamine and 400 parts of methanol was stirred and refluxed overnight. Another portion of 40 parts of O-ethyl 1-(phenylmethyl)-4-piperidineethanimidate hydrochloride was added and stirring was continued for 4 hours at reflux. The reaction mixture was evaporated. Water was added to the residue. The solution was treated with ammonium hydroxide. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 74.5 parts (63%) of 1-[(4-methylphenyl)methyl]-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazole; mp. 124.2° C. (6).