Triethylamine → 1-Ethyl-2-(methylaminomethyl)-1H-indole

HRID 1761079ノート

反応式

HRID 1761079 の反応式
[CH2:1](OC(ON1C(=O)CCC1=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[C:27]([N:29]([CH2:31][C:32]1[NH:33][C:34]2C(C=1)=CC=C[CH:35]=2)C)=O)C1C=CC=CC=1.CNCC1NC2C(C=1)=CC=CC=2.C(N(CC)CC)C>CN(C=O)C>[CH2:34]([N:33]1[C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:1]=[C:32]1[CH2:31][NH:29][CH3:27])[CH3:35]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 11194490N-Methyl-1H-indole-2-methanamineHCID 867595922-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole N-(Benzyloxycarbonyloxy)succinimide

生成物 1

HCID 225937291-Ethyl-2-(methylaminomethyl)-1H-indole収率 114.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole N-(Benzyloxycarbonyloxy)succinimide (17.10 g, 68.6 mmole) was added to a solution of 2-(methylaminomethyl)-1H-indole (10.00 g, 62.4 mmole), from Preparation 33, and triethylamine (9.60 mL, 68.6 mmole) in DMF (100 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and the mixture was extracted with ethyl acetate. The combined extracts were dried over K2CO3 and concentrated. Flash chromatography on silica gel (20% ethyl acctate/hexanes) gave the title compound (14.80 g, 80%) as an off-white solid: MS (ES) m/e 295 (M+H)+.

後処理

  1. concentrationthen was concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over K2CO3
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-dae1744b35634718bb051636c58c2a94
出典データセット
uspto-grants-2005_01
特許番号
US06846819B1

反応ノート

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