Diethyl Ether → (3R)-1-(2-(4-chlorophenyl)-2-oxoethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 404616Notes

Reaction equation

HRID 404616 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[C:12]1([CH:18]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]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])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCOCC>C(OCC)(=O)C>[Br-:1].[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N+:24]23[CH2:25][CH2:26][CH:27]([CH2:28][CH2:29]2)[C@@H:22]([O:21][C:19](=[O:20])[CH:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)[CH2:23]3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 68303p-Chlorophenacyl bromideHCID 71603247(R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate

Product 1

HCID 86688875(3R)-1-(2-(4-chlorophenyl)-2-oxoethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromideYield 79.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(4-chlorophenyl)ethanone (49.8 mg, 0.21 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate (70 mg, 0.21 mmol) in ethyl acetate (2 ml). The reaction was stirred at room temperature overnight (UPLC-MS: complete conversion). Et2O (1 ml) was added and the white precipitate was collected by suction filtration and dried under vacuum to obtain (3R)-1-(2-(4-chlorophenyl)-2-oxoethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (93.5 mg, 78% yield) as a white solid.

Workup

  1. filtrationthe white precipitate was collected by suction filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-ead0601e0c364723be382b92c0c9918e
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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