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

HRID 565838

Reaction equation

HRID 565838 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-21facdac264045f58d490afc4eccbf74
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Linked notes

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