2-Azidomethyl-1-benzylpyrrolidine → (1-Benzylpyrrolidin-2-yl)methanamine

HRID 2035526Notes

Reaction equation

HRID 2035526 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[N+]=[N-]>C(O)C.[C].[Pd]>[NH2:1][CH2:4][CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 122753532-Azidomethyl-1-benzylpyrrolidine

Product 1

HCID 9855700(1-Benzylpyrrolidin-2-yl)methanamineYield 91.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

668.5 mg of the 2-azidomethyl-1-benzylpyrrolidine crude product obtained was dissolved in 5 mL of ethanol, to which 160 mg of 10% palladium carbon was added, and stirred at room temperature under an atmosphere of hydrogen gas for 5 hours. The 10% palladium carbon was celite-filtered, and the filtered product was washed with methanol. The solvent was evaporated, and the residue was purified by silica gel chromatography (chloroform to chloroform:methanol=30:1 to chloroform:methanol=15:1) to obtain 539.7 mg of the title compound crude product as a light yellow oil. Without further purification, this was used as the feed material for the next reaction.

Workup

  1. additionwas added
  2. filtrationThe 10% palladium carbon was celite-filtered
  3. washthe filtered product was washed with methanol
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel chromatography (chloroform to chloroform:methanol=30:1 to chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-f1fea1c135b4422cb52fc69f3a094ff3
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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