Reaktion #5597

Reaktionsgleichung

Potassium hydroxide

3-aminoquinuclidine dihydrochloride

sodium chloride

chloroacetyl chloride

→

solid

Ausbeute 144.0%

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

Ausbeute 144.0%

Lösungsmittel

water

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle