Hydrochloric Acid → 5-Phenyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one

HRID 1679359Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].O[CH2:6][NH:7][C:8](=[O:23])[CH2:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[N+](C1C=CC=CC=1)([O-])=O.Cl>O>[C:11]1([CH:10]2[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:6][NH:7][C:8](=[O:23])[CH2:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

8.7 g. (0.065 moles) of aluminium chloride are added to a solution of 7.7 g. (0.030 moles) of N-hydroxymethyl-3,3-diphenyl-propionamide in 300 ml. of nitrobenzene. The reaction mixture is heated, with stirring, at 100° C. for 6 hours and then cooled and poured into 1 liter water containing 5 ml. of concentrated hydrochloric acid. The nitrobenzene is removed by steam distillation and the residue is extracted with chloroform. The organic phase is dried over anhydrous sodium sulfate and then evaporated to dryness. The residual solid is purified by chromatography on a silica column, using a mixture of benzene and ethanol (85:15 v/v) as eluent, and then recrystallized from 2-propanol. 2.4 g. (34% of theory) of 5-phenyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one are obtained. M.P. 182°-183° C.

Workup

temperatureThe reaction mixture is heated
temperaturecooled
customThe nitrobenzene is removed by steam distillation
extractionthe residue is extracted with chloroform
dry with materialThe organic phase is dried over anhydrous sodium sulfate
customevaporated to dryness
customThe residual solid is purified by chromatography on a silica column
additiona mixture of benzene and ethanol (85:15 v/v) as eluent
customrecrystallized from 2-propanol

Sources & evidence

ORD record: ord-28b9cf4ca4b74d13a60ea29f22c2ce21
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04080449

Reaction notes

Loading…