1-(4-Nitrobenzyl)pyrrolidine → 4-(Pyrrolidin-1-ylmethyl)aniline

HRID 2228036Notes

Reaction equation

HRID 2228036 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 7835221-(4-Nitrobenzyl)pyrrolidine

Product 1

HCID 7768524-(Pyrrolidin-1-ylmethyl)anilineYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (100 ml) was dissolved 1—(4-nitrobenzyl)-pyrrolidine (23.5 g), and to the mixture was added dried 10% palladium on carbon (1.00 g). Under hydrogen atmosphere, the mixture was stirred at room temperature under atmospheric pressure for 20 hours. The palladium was filtered off, and the filtrate was concentrated. The residue was separated and purified with column chromatography (ethyl acetate/triethylamine=10/1) to give 1—(4-aminobenzyl)pyrrolidine (8.54 g) as orange oil.

Workup

  1. additionto the mixture was added
  2. dry with materialdried 10% palladium on carbon (1.00 g)
  3. filtrationThe palladium was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/triethylamine=10/1)

Sources & evidence

ORD record
ord-442f71f070ec40c5b5cd58800c747e34
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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