HCID 68967238, compound → 2-(pyrrolidin-1-ylmethyl)aniline

HRID 2376163Notes

Reaction equation

HRID 2376163 reaction equation
C([CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O)C>[Pd].CO>[N:4]1([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])[CH2:5][CH2:6][CH2:7][CH2:3]1

Participants

4

Reactant 1

HCID 68967238HCID 68967238, compound

Product 1

HCID 2643112-(pyrrolidin-1-ylmethyl)anilineYield 115.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl 1-(2-nitrobenzyl)pyrrolidine (1.90 g) and 10% palladium on carbon (200 mg) in methanol (40 mL) was hydrogenated at ambient temperature. After completion of the reaction, the catalyst in the reaction mixture was removed by filtration. The solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform/methanol=20/1 v/v) to give [2-(1-pyrrolidinylmethyl)phenyl]amine (1.65 g) as a pale yellow solid.

Workup

  1. customwas hydrogenated at ambient temperature
  2. customAfter completion of the reaction
  3. customthe catalyst in the reaction mixture was removed by filtration
  4. customThe solvent was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=20/1 v/v)

Sources & evidence

ORD record
ord-af209a647af441289dcc1e5da739eb1a
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

Loading…