Sodium Chloride → 3-Quinuclidinone oxime

HRID 2243815Notes

Reaction equation

HRID 2243815 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=O)[CH2:3]2.Cl.[NH2:12][OH:13].CC(O[Na])=O.O.O.O.[Na+].[Cl-]>O>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[N:12][OH:13])[CH2:3]2

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 443297Hydroxyamine hydrochlorideHCID 178476686sodium;acetate;trihydrate

Product 1

HCID 2974083-Quinuclidinone oximeYield 107%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

32.33 g (200 mmol) of 3-Quinuclidinone hydrochloride was dissolved in 75 ml of water, and to the solution of hydroxylamine hydrochloride (16.4 g; 236 mmol) and CH3CO2Na.3H2O (80 g; 588 mmol) was added. The mixture was stirred at 70° C. for 1 hour. Then NaCl (10 g) was dissolved in the mixture and was cooled to 0° C. Separated crystals were filtered and carefully dried. The obtained crude 3-quinuclidone oxime (approx. 30 g) was used in the next step of the synthesis without further purification.

Workup

  1. temperaturewas cooled to 0° C
  2. customSeparated crystals
  3. filtrationwere filtered
  4. customcarefully dried

Sources & evidence

ORD record
ord-4efd74f2ec094c0d89af2753a073bbfa
Source dataset
uspto-grants-2010_03
Patent number
US07678788B2

Reaction notes

Loading…