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

HRID 2081242Notes

Reaction equation

HRID 2081242 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.[CH2:14]([O:16][NH2:17])[CH3:15]>CO>[ClH:1].[CH2:14]([O:16][N:17]=[C:2]([CH:5]1[CH:10]2[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]2)[CH2:6]1)[CH3:3])[CH3:15]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 197994593-Acetyl quinuclidine hydrochloride

Product 1

HCID 86744768(1-azabicyclo-[2,2,2]-octan-3-yl)-ethanone O-ethyloxime hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.9 g of 3-acetyl quinuclidine hydrochloride and 0.98 g of O-ethylhydroxylamine hydrochloride are heated for 20 minutes to reflux in 30 cm3 of methanol, followed by concentrating to dryness and purifying by chromatography on alumina (eluant: methylene chloride-methanol 9-1). The reaction medium is acidified using gaseous hydrochloric acid, then evaporated to dryness. After crystallizing from ethanol, filtering, and rinsing with ether, 1.3 g of expected product is recovered. M.p.=198°-200° C.

Workup

  1. concentrationby concentrating to dryness
  2. custompurifying by chromatography on alumina (eluant: methylene chloride-methanol 9-1)
  3. customevaporated to dryness
  4. customAfter crystallizing from ethanol
  5. filtrationfiltering
  6. washrinsing with ether, 1.3 g of expected product
  7. customis recovered

Sources & evidence

ORD record
ord-e2079ee0f6104709a5d0ce29c2d23382
Source dataset
uspto-grants-1993_02
Patent number
US05183893

Reaction notes

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