Triethylamine → 2-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole

HRID 1921001Notes

Reaction equation

HRID 1921001 reaction equation
[CH2:1]([O:8][C:9]([O:11]N1C(=O)CCC1=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][NH:20][CH2:21][C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([O:8][C:9]([N:20]([CH2:21][C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:19])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 11194490N-Methyl-1H-indole-2-methanamine

Product 1

HCID 574408432-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1H-indoleYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 acetate/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-95f8a04461584f47a9236c9f2e509a37
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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