2-Chloroacetophenone → HCID 86688899, compound

HRID 404640Notes

Reaction equation

HRID 404640 reaction equation
[C:1]1([CH:7]([N:19]2[CH2:24][CH2:23][S:22][CH2:21][CH2:20]2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28]>C(OCC)(=O)C>[Cl-:25].[O:28]=[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:26][N+:13]12[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]1)[C@@H:11]([O:10][C:8](=[O:9])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[N:19]1[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1)[CH2:12]2

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 86688898HCID 86688898, compound

Product 1

HCID 86688899HCID 86688899, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-quinuclidin-3-yl 2-phenyl-2-thiomorpholinoacetate (68 mg, 0.20 mmol) was dissolved in ethyl acetate (2 ml) and 2-chloro-1-phenylethanone (33.4 mg, 0.22 mmol) was added. The solution was stirred at room temperature for two days. The solvent was evaporated and the residue was triturated with Et2O. The suspension was filtered on a buckner funnel to obtain (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-thiomorpholinoacetoxy)-1-azoniabicyclo[2.2.2]octane chloride (89 mg, 0.178 mmol, 91% yield) as an off-white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. filtrationThe suspension was filtered on a buckner funnel

Sources & evidence

ORD record
ord-88fad6527501490f9877dfd12f02efae
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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