Phenacyl bromide → (3R)-3-(2-(4-chlorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 404680Notes

Reaction equation

HRID 404680 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])=[CH:4][CH:3]=1.[Br:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]>C(#N)C>[Br-:26].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N+:14]([CH2:27][C:28](=[O:29])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 86688939HCID 86688939, compound

Product 1

HCID 86688940(3R)-3-(2-(4-chlorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 63.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-quinuclidin-3-yl 2-(4-chlorophenyl)-2-(piperidin-1-yl)acetate (100 mg, 0.28 mmol) and 2-bromo-1-phenylethanone (60.3 mg, 0.30 mmol) were dissolved in acetonitrile (4 ml) and stirred at room temperature for 16 hours. The solvent was evaporated and the resulting residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-3-(2-(4-chlorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (98 mg, 63.3% yield) as white powder.

Workup

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

Sources & evidence

ORD record
ord-9aab93d2271f477c9a6681b00c76579a
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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