4-(4-Pyrrolidin-1-ylcarbonylbenzyl)-nitrobenzene → 4-[4-(1-Pyrrolidinecarbonyl)benzyl]-phenylamine

HRID 993398Notes

Reaction equation

HRID 993398 reaction equation
[N:1]1([C:6]([C:8]2[CH:23]=[CH:22][C:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[N:1]1([C:6]([C:8]2[CH:23]=[CH:22][C:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)=[CH:10][CH:9]=2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 120943914-(4-Pyrrolidin-1-ylcarbonylbenzyl)-nitrobenzene

Product 1

HCID 120943904-[4-(1-Pyrrolidinecarbonyl)benzyl]-phenylamineYield 102.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(4-pyrrolidin-1-ylcarbonylbenzyl)-nitrobenzene (202 mg, 065 mmol), 10% palladium on carbon (110 mg), and ethanol (20 mL) was hydrogenated at 40 psi for 16 hours. The mixture was filtered through a Celite pad, and solvents evaporated to give 4-[4-(1-pyrrolidinecarbonyl)benzyl]-phenylamine as a white solid (187 mg, 99%).

Workup

  1. filtrationThe mixture was filtered through a Celite pad, and solvents
  2. customevaporated

Sources & evidence

ORD record
ord-369f1d6ab122456a9f55b11d22415333
Source dataset
uspto-grants-2002_10
Patent number
US06472536B1

Reaction notes

Loading…