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

HRID 2112656Notes

Reaction equation

HRID 2112656 reaction equation
C(O[C:9]([N:11]([CH2:13][C:14]1[N:15]([CH2:23][CH3:24])[C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)C)=O)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[CH2:23]([N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[C:14]1[CH2:13][NH:11][CH3:9])[CH3:24]

Participants

4

Reactant 1

HCID 225937652-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1-ethyl-1H-indole

Product 1

HCID 225937291-Ethyl-2-(methylaminomethyl)-1H-indoleYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

2-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1-ethyl-1H-indole (1.30 g, 4.0 mmole) was added to a suspension of Pearlman's catalyst (about 0.30 g) in MeOH at RT in a Parr flask. The reaction was placed under 50 p.s.i. of H2 and shaken for 8 hr. The mixture was filtered through Celite® and the filter pad was washed with MeOH. The filtrate was concentrated to afford the title compound (0.75 g, 100%) as a light yellow solid: MS (ES) m/e 189 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washthe filter pad was washed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-698c5d7a99ec4da787734a8220399204
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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