Sodium Hydroxide → 2H-benzazepine

HRID 1630694노트

반응식

HRID 1630694 반응식
N1([C:7]2[CH:17]=[CH:16][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][NH:15][C:9]=3[CH:8]=2)CCOCC1.[OH-].[Na+]>CO>[N:15]1[CH2:14][CH:13]=[CH:12][CH:11]=[C:10]2[CH:16]=[CH:17][CH:7]=[CH:8][C:9]=12

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 669638998-Morpholinobenzazepine

생성물 1

HCID 866101862H-benzazepine수율 192.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of the N-acetyl benzazepine (0.14 g, 0.40 mmol) from step I above in methanol (10 mL) was added an aqueous 2 N solution of sodium hydroxide (10 mL). The reaction solution was heated under reflux for 72 hours and then cooled to room temperature. The resultant reaction mixture was extracted with dichloromethane, washed with water and aqueous saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The residue obtained was purified by flash column chromatography (dichloromethane to 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide) to give the desired 2H-benzazepine (0.11 g, 89%) as a white foam: 1H NMR (DMSO-d6, 500 MHz) δ 7.35 (t, J=7.5 Hz, 2H), 7.24 (t, J=7.5 Hz, 1H), 7.14 (d, J=7.5 Hz, 2H), 6.84 (d, J=2.5 Hz, 1H), 6.65-6.60 (m, 1H), 6.49-6.38 (br, 1H), 4.33 (d, J=8.5 Hz, 1H), 3.95 (d, J=14.5 Hz, 1H), 3.77 (d, J=14.5 Hz, 1H), 3.71 (t, J=5.0 Hz, 4H), 3.10-2.87 (m, 6H), 2.21-2.12 (m, 1H), 2.03-1.85 (m, 1H).

후처리

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 72 hours
  3. customThe resultant reaction mixture
  4. extractionwas extracted with dichloromethane
  5. washwashed with water and aqueous saturated sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue obtained
  9. customwas purified by flash column chromatography (dichloromethane to 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide)

출처 및 근거

ORD 기록
ord-7daef4bb550140deab6f4536170e54c7
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791101B2

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