Dimethylamine → Indolo(1,7-ab)(1)benzazepine-1-ethanamine, 6,7-dihydro-N,N,2-trimethyl-

Participants

Reaction Conditions

Reaction Steps

2.34 ml (1.5 × 0.0085 mol) of 5.4-N ethanolic dimethylamine was added, below the surface and with cooling, to 13.6 ml of glacial acetic acid. 0.95 ml (1.5 × 0.0085 mol) of a 40% formaldehyde solution were also added, followed by 2.1 g (0.0085 mol) of 6,7-dihydro-1,2-dimethylindolo[1,7-ab][1]benzazepine. The mixture was heated for 7 hours at 90° C, evaporated in vacuo and taken up in water and ether. The ether was separated and extracted with 2-N hydrochloric acid. The combined acid/aqueous extracts were made alkaline and extracted with ether. The latter ether extract was evaporated and distilled at ca 130° C (air-bath temperature)/10-4 mm Hg to give 1.8 g (69.5% yield) of 1-(2-dimethylaminoethyl)-6,7-dihydro-2-methylindolo[1,7-ab][1]benzazepine whose oxalate melted at 154°-155° C.

Provenance & Evidence