Sodium Hydroxide → 5,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepine

HRID 888095노트

반응식

HRID 888095 반응식
[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][C:6](=O)[NH:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O.C1COCC1>[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][CH2:6][NH:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1=2

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2회HCID 570064745,5-Dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

생성물 1

HCID 574702555,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepine

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

5,5-Dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (1.5 g, 8.0 mmol) was dissolved into THF (20 ml) and cooled down to 0° C. LAH (0.5 g 60% in oil, 13 mmol) was added in portions. The reaction was heated to reflux for 2 h. TLC showed a new spot alongside staring lactam. Another 360 mg of LAH was added and the mixture was heated for 2 h. H2O was added until sizzling stopped followed by 2N NaOH. Stirred for 15 min at RT. Na2SO4 (3.8 g) was added and the mixture was stirred for 15 min followed by filtration over Celite®. Diluted with EtOAc and washed with H2O, dried (MgSO4), filtered and concentrated to give 5,5-Dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 h
  3. temperaturethe mixture was heated for 2 h
  4. stirringthe mixture was stirred for 15 min
  5. filtrationfollowed by filtration over Celite®
  6. additionDiluted with EtOAc
  7. washwashed with H2O
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9d0d82ddc0e04ca0a25d7e7b44c8bde8
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247556B2

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