Sodium Hydroxide → 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

HRID 609733

반응식

HRID 609733 반응식
[OH-].[Na+].[O:3]1[CH:8]=[CH:7][CH:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14](C(=O)C2C=CC=CC=2)[CH:13]=[C:12]3[CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[CH2:5][CH2:4]1>CO>[NH3:14].[O:3]1[CH:4]=[CH:5][CH:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[C:12]3[CH2:26][CH2:27][N:28]([CH3:29])[CH3:30])[CH2:7][CH2:8]1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 196004485-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

생성물 2

HCID 222Ammonia수율 10%HCID 196004255-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole수율 141.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

An aqueous solution of sodium hydroxide (2M, 1 mL, 2 mmol) was added to 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (30 mg, 0.08 mmol) in methanol (2 mL) and the resulting solution was stirred at room temperature for 16 h. The reaction mixture was partitioned between water and ethyl acetate, washed with brine, dried over sodium sulfate and the solvent was removed in vacuo. Preparative thin layer chromatography (silica gel, 10% 2M methanolic ammonia in dichloromethane) yielded 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (15.3 mg, 70%); HRMS-FAB+ for C17H22N2O: calculated MH+ :271.18103; found MH+ :271.18177.

후처리

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-f7644bf8f2e14e5d9929e4671f6fde81
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998438

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