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

HRID 1679359노트

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HRID 1679359 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7416NitrobenzeneHCID 6451240Aluminum(III) ChlorideHCID 20362665N-(Hydroxymethyl)-β-phenylbenzenepropanamide

생성물 1

HCID 199031995-phenyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one수율 34%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-28b9cf4ca4b74d13a60ea29f22c2ce21
출처 데이터셋
uspto-grants-1978_03
특허 번호
US04080449

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