Allyl bromide → HCID 22904998, 화합물

HRID 865335

반응식

HRID 865335 반응식
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[C:5]=2[CH:4]=1.[H-].[Na+].[CH2:17](Br)[CH:18]=[CH2:19]>CN(C)C=O.[Cl-].[Na+].O>[CH2:19]([N:10]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[C:11]1=[O:12])[CH:18]=[CH2:17]

참가 물질

6

반응물 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 112755298-Methoxy-2,3,4,5-tetrahydro-benzo[c]azepin-1-one

생성물 1

HCID 22904998HCID 22904998, 화합물수율 83%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

A solution of 8-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (10.0 g, 0.052 mol) in N,N-dimethylformamide (30 mL) and allylbromide (23 mL, 0.260 mL) was treated with NaH (60% by wt. dispersion in oil, 2.50 g, 0.063 mol) and the resulting grey suspension stirred at room temperature under an atmosphere of argon. Gas evolution was noted. After 15 minutes, the solution was diluted with brine and partitioned between ethyl acetate and brine. The combined organic layers were concentrated in vacuo and purified by chromatography over silica gel eluting with a gradient of hexane to 1:1 ethyl acetate/hexane to yield 8 g (83%) of 2-allyl-8-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one as a colorless oil: 1H NMR(CDCl3) d7.23(m, 1H), 7.03(d, J=9 Hz, 1H), 6.90(dd, J=3, 9 Hz, 1H), 5.91(m, 1H), 5.23(m, 2H), 4.20(d, J=6 Hz, 2H), 3.82(s, 3H), 3.18(t, J=6 Hz, 2H), 2.72(t, J=6 Hz, 2H), 1.96(pentet, J=6 Hz, 2H); 13C NMR(CDCl3) d170.59(CO), 158.42(NCO), 136.88, 133.81, 129.43, 129.35, 129.33, 117.56, 117.54, 112.98, 55.26, 49.43, 45.37, 29.57, 29.22; MS(FAB)m/z=232.1(MH+).

후처리

  1. custompartitioned between ethyl acetate and brine
  2. concentrationThe combined organic layers were concentrated in vacuo
  3. custompurified by chromatography over silica gel eluting with a gradient of hexane to 1:1 ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-e6f7f3710ee24f37b0079fd5a8625732
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565449

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