HCID 11391343, compound → HCID 11148957, compound

HRID 658447Notes

Reaction equation

HRID 658447 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-])=O)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]>CCO.[Pd]>[CH2:18]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH2:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:19]

Participants

4

Reactant 1

HCID 11391343HCID 11391343, compound

Product 1

HCID 11148957HCID 11148957, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Diethyl-[2-(5-nitroindol-1-yl)ethyl]amine (1.6 g, 6.1 mmol) was dissolved in absolute EtOH (100 mL) and syringed into a flask containing 10% Pd over carbon (160 mg) under an argon atmosphere. The reaction mixture was placed under H2 atmosphere (1 Atm pressure) and stirred at RT for 3 h. The reaction was filtered over a Celite pad and washed well with EtOH. Evaporation of the volatile solvent gave the title compound (1.4 g, 99%) as a brown solid. TLC (10% MeOH/DCM), Rf=0.20; LC MS m/z 232.3 (MH+).

Workup

  1. customsyringed into a flask
  2. filtrationThe reaction was filtered over a Celite pad
  3. washwashed well with EtOH
  4. customEvaporation of the volatile solvent

Sources & evidence

ORD record
ord-ec909e7b83ba4208a75a73a8604e3d10
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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