Reaction #5597

Reaction equation

Potassium hydroxide

3-aminoquinuclidine dihydrochloride

sodium chloride

chloroacetyl chloride

→

solid

Yield 144.0%

N-1-Azabicyclo[2.2.2]oct-3-yl-2-chloroacetamide, monohydrochloride

Yield 144.0%

Solvents

water

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Otherthe layers separated
2. 2
   WashThe aqueous layer was washed with methylene chloride (2×75 ml)
3. 3
   Dryingdried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   workup.STIRRINGthe mixture stirred overnight
6. 6
   OtherThe solvent was removed on a rotary evaporator
7. 7
   OtherThe residue was recrystallized from methanol-ethyl acetate

Procedure

Potassium hydroxide (10 g) was added to a solution of 3-aminoquinuclidine dihydrochloride (10.45 g, 0.052 mole) in water (80 ml) saturated with sodium chloride. After stirring for 30 minutes, methylene chloride (75 ml) was added and the layers separated. The aqueous layer was washed with methylene chloride (2×75 ml), and the extracts combined with the methylene chloride layer above; dried over sodium sulfate, filtered, and the volume reduced to 100 ml. A solution of chloroacetyl chloride (3.11 g, 0.0273 mole) in methylene chloride (25 ml) was added dropwise and the mixture stirred overnight. The solvent was removed on a rotary evaporator. The residue was recrystallized from methanol-ethyl acetate to give a white solid (4.7 g), m.p. ca. 189°-195° C. The structure was confirmed by NMR.

Source