2-Chloroacetophenone → HCID 86688917, compound

HRID 404658Notes

Reaction equation

HRID 404658 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[F:11][C:12]1([F:36])[CH2:17][CH2:16][N:15]([CH:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:19]([O:21][C@@H:22]2[CH:27]3[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]3)[CH2:23]2)=[O:20])[CH2:14][CH2:13]1>C(OCC)(=O)C>[Cl-:1].[F:36][C:12]1([F:11])[CH2:17][CH2:16][N:15]([CH:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:19]([O:21][C@@H:22]2[CH:27]3[CH2:26][CH2:25][N+:24]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:29][CH2:28]3)[CH2:23]2)=[O:20])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 86688916HCID 86688916, compound

Product 1

HCID 86688917HCID 86688917, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (31.0 mg, 0.20 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(4,4-difluoropiperidin-1-yl)-2-phenylacetate (24b) (73 mg, 0.20 mmol) in ethyl acetate (3 ml). The reaction was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was triturated with Et2O (4 ml). A white precipitate was formed and it was collected by suction filtration and dried under vacuum at 40° C. overnight, to obtain (3R)-3-(2-(4,4-difluoropiperidin-1-yl)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (81 mg, 78% yield).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was triturated with Et2O (4 ml)
  3. customA white precipitate was formed
  4. filtrationit was collected by suction filtration
  5. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-abba4528e0db4dde953cfb67e9f46e05
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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