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

HRID 1277018

Reaction equation

HRID 1277018 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-0ecdbbb4347949079b6be9802c9695f8
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Linked notes

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