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

HRID 226464Notes

Reaction equation

HRID 226464 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-6edb1bc5f79b4f11b8fe30c71c1e594f
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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