2-Chloroacetophenone → HCID 86688906, compound

HRID 404648Notes

Reaction equation

HRID 404648 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]([O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[O:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>CCOC(C)=O.C(#N)C>[Cl-:28].[C:1]([N:4]1[CH2:5][CH2:6][N:7]([CH:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]([O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N+:16]([CH2:29][C:30](=[O:31])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([CH2:17][CH2:18]3)[CH2:15]2)=[O:12])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 107572-ChloroacetophenoneHCID 86688905HCID 86688905, compound

Product 1

HCID 86688906HCID 86688906, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-Quinuclidin-3-yl 2-(4-acetylpiperazin-1-yl)-2-phenylacetate (210 mg, 0.56 mmol) was dissolved in a mixture EtOAc (3.8 ml) and acetonitrile (1.8 ml). 2-Chloro-1-phenylethanone (96 mg, 0.62 mmol) was added and the reaction was stirred at room temperature for 16 hours. The solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-3-(2-(4-acetylpiperazin-1-yl)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (178 mg, 59.9% 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-ffae28f55c874bae9b1e7502e39e2d00
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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