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

HRID 466662Notes

Reaction equation

HRID 466662 reaction equation
[OH-].[K+].Cl.Cl.[NH2:5][CH:6]1[CH:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1.[Cl-].[Na+].[Cl:16][CH2:17][C:18](Cl)=[O:19]>O.C(Cl)Cl>[ClH:16].[N:8]12[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9]1)[CH:6]([NH:5][C:18](=[O:19])[CH2:17][Cl:16])[CH2:7]2

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6577Chloroacetyl chlorideHCID 14797Potassium HydroxideHCID 197853Quinuclidine, 3-amino-, dihydrochloride

Product 1

HCID 131716900N-1-Azabicyclo[2.2.2]oct-3-yl-2-chloroacetamide, monohydrochlorideYield 144%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

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.

Workup

  1. customthe layers separated
  2. washThe aqueous layer was washed with methylene chloride (2×75 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. stirringthe mixture stirred overnight
  6. customThe solvent was removed on a rotary evaporator
  7. customThe residue was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-b1530e3483ea49ad866451d5d0d96430
Source dataset
uspto-grants-1992_10
Patent number
US05157053

Reaction notes

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