6-[4-(4-(5-Nitroindol-3-yl)butyl)piperazino]-1,4-benzodioxane → 6-[4-(4-(5-Aminoindol-3-yl)butyl)piperazino]-1,4-benzodioxane

HRID 4959Notes

Reaction equation

HRID 4959 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:32]=[CH:31][C:26]3[O:27][CH2:28][CH2:29][O:30][C:25]=3[CH:24]=2)[CH2:19][CH2:18]1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:32]=[CH:31][C:26]3[O:27][CH2:28][CH2:29][O:30][C:25]=3[CH:24]=2)[CH2:21][CH2:22]1

Participants

4

Reactant 1

HCID 197973246-[4-(4-(5-Nitroindol-3-yl)butyl)piperazino]-1,4-benzodioxane

Product 1

HCID 197973406-[4-(4-(5-Aminoindol-3-yl)butyl)piperazino]-1,4-benzodioxane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3.8 g of 6-[4-(4-(5-nitroindol-3-yl)butyl)piperazino]-1,4-benzodioxane in 45 ml of methanol is hydrogenated with stirring on 0.1% Pd-C at 20° and 1 bar until absorption of H2 is complete. The mixture is poured into ice-water, worked up in the conventional manner and gives 6-[4-(4-(5-aminoindol-3-yl)butyl)piperazino]-1,4-benzodioxane.

Workup

  1. custom1 bar until absorption of H2
  2. additionThe mixture is poured into ice-water

Sources & evidence

ORD record
ord-e38ff13a85fc45659c62ccbd6fef9407
Source dataset
uspto-grants-1993_09
Patent number
US05242925

Reaction notes

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