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

HRID 1729719Notes

Reaction equation

[CH3:1][NH:2][CH3:3].C=O.[CH3:6][C:7]1[N:15]2[C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[CH2:18][CH2:19][C:13]3=[C:14]2[C:9](=[CH:10][CH:11]=[CH:12]3)[C:8]=1[CH3:24].[C:25]([O-])(=O)C([O-])=O>C(O)(=O)C>[CH3:1][N:2]([CH3:25])[CH2:3][CH2:6][C:7]1[N:15]2[C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[CH2:18][CH2:19][C:13]3=[C:14]2[C:9](=[CH:10][CH:11]=[CH:12]3)[C:8]=1[CH3:24]

Participants

Conditions

Temperature: 90 °C

Procedure

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.

Workup

customevaporated in vacuo
customThe ether was separated
extractionextracted with 2-N hydrochloric acid
extractionextracted with ether
extractionThe latter ether extract
customwas evaporated
distillationdistilled at ca 130° C (air-bath temperature)/10-4 mm Hg

Sources & evidence

ORD record: ord-82c5c1fe1976466dadac0a2940b7465c
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03989717

Reaction notes

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