HCID 86747426, compound → HCID 19108409, compound

HRID 327385Notes

Reaction equation

HRID 327385 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[C:10](=[N:11]O)[CH:9]2[CH2:13][CH2:14][N:6]1[CH2:7][CH2:8]2)[CH3:3]>[Ni].C(O)C>[CH3:3][N:2]([CH2:4][CH:5]1[CH:10]([NH2:11])[CH:9]2[CH2:13][CH2:14][N:6]1[CH2:7][CH2:8]2)[CH3:1]

Participants

4

Reactant 1

HCID 86747426HCID 86747426, compound

Product 1

HCID 19108409HCID 19108409, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(dimethylaminomethyl)-1-azabicyclo[2.2.2]octan-3-one oxime (3.55 g, 18 mmoles) in reagent grade ethanol (150 ml) was treated with Raney Nickel and hydrogenated in a Parr apparatus at room temperature and 55-58 psi for 18 hours. The product solution was filtered through Celite®, concentrated in vacuo, and subjected to bulb-to-bulb distillation (bp 100°-120° C. at 0.30 mm Hg) to provide 2.57 g (78%) of a colorless oil. The product was shown to be a mixture of cis:trans (1:3) isomers by nmr and glc analysis.

Workup

  1. filtrationThe product solution was filtered through Celite®
  2. concentrationconcentrated in vacuo
  3. distillationsubjected to bulb-to-bulb distillation (bp 100°-120° C. at 0.30 mm Hg)

Sources & evidence

ORD record
ord-c3482c283d4e4b3db76697ae0319909f
Source dataset
uspto-grants-1993_12
Patent number
US05273972

Reaction notes

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