3-[N-(Benzyloxycarbonyl)-N-methylaminomethyl)-1-benzyl-1H-indole → 1-benzyl-3-(methylaminomethyl)-1H-indole

HRID 1921028Notes

Reaction equation

HRID 1921028 reaction equation
C(O[C:9]([N:11]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:15]=1)C)=O)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[CH2:23]([N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([CH2:13][NH:11][CH3:9])=[CH:15]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 221390153-[N-(Benzyloxycarbonyl)-N-methylaminomethyl)-1-benzyl-1H-indole

Product 1

HCID 122838761-benzyl-3-(methylaminomethyl)-1H-indoleYield 86.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

3-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1-benzyl-1H-indole (0.9 g, 2.3 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 5 hr. The mixture was filtered through Celite® and the filter pad was washed with MeOH. The filtrate was concentrated to afford the title compound (0.5 g, 86%) as a light yellow solid: MS (ES) m/e 251 (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-abe470d76a1143939113d4677207d713
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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