Sodium Hydroxide → 8-Bromo-1,4-dimethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 84112노트

반응식

HRID 84112 반응식
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:19])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH:6]1[CH3:20])=O.[OH-].[Na+]>CO.O>[Br:19][C:14]1[C:15]([O:17][CH3:18])=[CH:16][C:8]2[CH2:7][CH:6]([CH3:20])[NH:5][CH2:11][CH:10]([CH3:12])[C:9]=2[CH:13]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 22292813N-Trifluoroacetyl-8-bromo-1,4-dimethyl-7-methoxy-2,3,4,5-tetrahydro 1H-3-benzazepine

생성물 1

HCID 101079168-Bromo-1,4-dimethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine수율 70.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of N-trifluoroacetyl-8-bromo-1,4-dimethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (21 mg, 0.055 mmol) in methanol (2 mL) was treated with 15% aqueous NaOH (2 mL), and stirred overnight at 20 C. The product mixture was diluted with water (5 mL), extracted twice with EtOAc (10 mL), the combined organic phases were washed with brine (10 mL), dried with Na2SO4 and concentrated to give 11 mg of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.29 (s, 1H), 6.64 (s, 1H), 3.88 (s, 3H), 3.02 (m, 2H), 2.89 (dd, J=9, 14 Hz, 1H), 2.80 (m, 1H), 2.67 (d, J=14 Hz, 1H), 2.53 (dd, J=10, 13, 1H) 1.30 (d, J=7 Hz, 3H), 1.19 (d, J=6 Hz, 3H). MS calculated for C13H18BrNO+H: 284, observed: 284.

후처리

  1. extractionextracted twice with EtOAc (10 mL)
  2. washthe combined organic phases were washed with brine (10 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6f7991f1af1547d883f95520d6d27ea1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846906B2

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