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

HRID 609733

反応式

HRID 609733 の反応式
[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

参加物

5

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f7644bf8f2e14e5d9929e4671f6fde81
出典データセット
uspto-grants-1999_12
特許番号
US05998438

関連ノート

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