O-Methylhydroxylamine hydrochloride → (1-azabicyclo-[2,2,2]-octan-3-yl)-ethanone O-methyloxime hydrochloride

HRID 2050891Notes

Reaction equation

HRID 2050891 reaction equation
[ClH:1].[C:2]([CH:5]1[CH:10]2[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]2)[CH2:6]1)(=O)[CH3:3].Cl.[CH3:14][O:15][NH2:16]>CO>[ClH:1].[CH3:14][O:15][N:16]=[C:2]([CH:5]1[CH:10]2[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]2)[CH2:6]1)[CH3:3]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 197994593-Acetyl quinuclidine hydrochloride

Product 1

HCID 86744766(1-azabicyclo-[2,2,2]-octan-3-yl)-ethanone O-methyloxime hydrochlorideYield 67.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.3 g of 3-acetyl quinuclidine hydrochloride (Helv. Chim. Acta (1963) 229, 2658) and 1.02 g of O-methylhydroxylamine hydrochloride are heated for 20 minutes to reflux in 30 cm3 of methanol. The solvent is evaporated and the residue is chromatographed on silica (eluant: chloroform-methanol 7-3). After crystallization from ethanol and from ether, 1.8 g of expected product is obtained. M.p.=186°-188° C.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is chromatographed on silica (eluant: chloroform-methanol 7-3)
  3. customAfter crystallization from ethanol

Sources & evidence

ORD record
ord-2e77574c63014939906a32918fd8cbd9
Source dataset
uspto-grants-1991_05
Patent number
US05015655

Reaction notes

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