2-(1-Pyrrolidinylmethyl)-1-azabicyclo[2.2.2]octan-3-one oxime → 2-(1-Pyrrolidinylmethyl)-1-azabicyclo[2.2.2]octan-3-amine

HRID 327388Notes

Reaction equation

HRID 327388 reaction equation
[N:1]1([CH2:6][CH:7]2[C:12](=[N:13]O)[CH:11]3[CH2:15][CH2:16][N:8]2[CH2:9][CH2:10]3)[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Ni]>[N:1]1([CH2:6][CH:7]2[CH:12]([NH2:13])[CH:11]3[CH2:10][CH2:9][N:8]2[CH2:16][CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 740017462-(1-Pyrrolidinylmethyl)-1-azabicyclo[2.2.2]octan-3-one oxime

Product 1

HCID 191084192-(1-Pyrrolidinylmethyl)-1-azabicyclo[2.2.2]octan-3-amineYield 87.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-(1-pyrrolidinylmethyl)-1-azabicyclo-[2.2.2]octan-3-one oxime (8.94 g, 40 mmoles) in methanol (250 ml) in a Parr bottle was treated with Raney Nickel and subjected to hydrogenation over 16 hours at 50-60 psi pressure. The resultant solution was filtered through Celite® under nitrogen, and concentrated in vacuo to provide 7.30 g (87%) of a colorless oil.

Workup

  1. filtrationThe resultant solution was filtered through Celite® under nitrogen
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1027ca3e9b594a659bf0c55084b41715
Source dataset
uspto-grants-1993_12
Patent number
US05273972

Reaction notes

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