Benzeneacetonitrile, 4-methoxy- → 2-(alpha-Cyano-4-methoxybenzylidene)perhydroazepine
Reaction equation
CO[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]=1.[CH3:10][O:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][C:17]#[N:18])=[CH:14][CH:13]=1.N12CCCCC1C=NCCC2>>[C:17]([C:16](=[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9]1)[C:15]1[CH:19]=[CH:20][C:12]([O:11][CH3:10])=[CH:13][CH:14]=1)#[N:18]Participants
4
Procedure
Stir 6.5 g of caprolactim methyl ether, 5.0 g of 4-methoxybenzyl cyanide and 0.5 g of 1,5-diazabicyclo[5.4.0]-undec-5-ene together under nitrogen for 18 hours at 125°. Then remove volatile components from the resulting reaction mixture under a high vacuum to obtain 2-(α-cyano-4-methoxybenzylidene)perhydroazepine as a viscous dark residue. Boil this residue with 50 ml of concentrated hydrochloric acid under reflux until the evolution of carbon dioxide ceases. Cool the refluxed material to ambient temperature, and then alkalize it (while cooling), extract the produced base with diethyl ether, dry the ether extract over sodium sulfate and concentrate the dried extract to obtain 2-(4-methoxybenzyl)-4,5,6,7-tetrahydro-3H-azepine. Hydrogenate this intermediate with platinum/active carbon/hydrogen in ethyl alcohol, filter off the catalyst, concentrate and then distil the filtrate to obtain the title compound with a BP of 100° to 106° at 0.01 mm of Hg.