5-benzyloxy-3-(2-nitro-propyl)-1H-indole → 1-methyl-2-(5-benzyloxy-1H-indol-3-yl)ethyl amine

HRID 6750Notes

Reaction equation

HRID 6750 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][CH:25]([N+:27]([O-])=O)[CH3:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(OCC)C>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][CH:25]([NH2:27])[CH3:26])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 140831715-benzyloxy-3-(2-nitro-propyl)-1H-indoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 151377401-methyl-2-(5-benzyloxy-1H-indol-3-yl)ethyl amineYield 51.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of lithium aluminum hydride (700 mg) in diethyl ether (25 mL) was slowly added a solution of 5-benzyloxy-3-(2-nitro-propyl)-1H-indole (650 mg) in diethyl ether (10 mL). The mixture was refluxed for 2 h. After cooling to rt, the reaction was quenched sequentially with 0.7 mL water, 0.7 mL 3 M aqueous sodium hydroxide, followed by 1.4 mL of water. The mixture was stirred at rt for 30 min and filtered. The filtrate was evaporated to afford 2-(5-benzyloxy-1H-indol-3-yl)-1-methyl-ethylamine (300 mg).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customthe reaction was quenched sequentially with 0.7 mL water, 0.7 mL 3 M aqueous sodium hydroxide
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-0c784588374a4ac3be3503b7507e6f15
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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