2-Chloroacetophenone → HCID 86688954, compound

HRID 404694Notes

Reaction equation

HRID 404694 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[N:11]1([CH:17]([C:29]2[CH:33]=[CH:32][S:31][CH:30]=2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CCOC(C)=O.C(#N)C>[Cl-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][N+:23]12[CH2:24][CH2:25][CH:26]([CH2:27][CH2:28]1)[C@@H:21]([O:20][C:18](=[O:19])[CH:17]([N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[C:29]1[CH:33]=[CH:32][S:31][CH:30]=1)[CH2:22]2

Participants

5

Reactant 2

HCID 107572-ChloroacetophenoneHCID 86688953HCID 86688953, compound

Product 1

HCID 86688954HCID 86688954, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (107 mg, 0.69 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(piperidin-1-yl)-2-(thiophen-3-yl)acetate (210 mg, 0.63 mmol) in EtOAc (4.2 ml) and acetonitrile (2.1 ml) and. The mixture was stirred at room temperature for 48 hours. The solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH=9/1) to collect the title compound (117 mg, 38.1% yield) as an off-white spongy solid.

Workup

  1. customThe solvent was evaporated
  2. customthe crude was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-f5e01e16eebd4c2e9af770c763c79cef
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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