2-Chloroacetophenone → HCID 86688948, compound

HRID 404688Notes

Reaction equation

HRID 404688 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1)=[O:11].[Cl:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30]>C(#N)C>[Cl-:27].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N+:15]([CH2:28][C:29](=[O:30])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([CH2:16][CH2:17]2)[CH2:14]1)=[O:11]

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 86688947HCID 86688947, compound

Product 1

HCID 86688948HCID 86688948, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-quinuclidin-3-yl 2-(2,4-difluorophenyl)-2-(piperidin-1-yl)acetate (275 mg, 0.75 mmol) and 2-chloro-1-phenylethanone (128 mg, 0.83 mmol) were dissolved in acetonitrile (8 ml) and stirred at room temperature overnight. The solvent was evaporated and the residue was triturated with Et2O and sonicated. The resulting precipitate was recovered by suction filtration and washed on the filter-paper with EtOAc and Et2O to obtain the title compound (261 mg, 66.6% yield) as a white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. customsonicated
  4. filtrationThe resulting precipitate was recovered by suction filtration
  5. washwashed on the
  6. filtrationfilter-paper with EtOAc and Et2O

Sources & evidence

ORD record
ord-a05d3ce9ac494529b14cc0b06c5adb37
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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