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

HRID 1761079Notes

Reaction equation

HRID 1761079 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-dae1744b35634718bb051636c58c2a94
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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