Diethyl Ether → (3R)-3-(2-(4-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 404684Notes

Reaction equation

HRID 404684 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[F:11][C:12]1[CH:17]=[CH:16][C:15]([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:14][CH:13]=1.CCOCC>CCOC(C)=O>[Cl-:1].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([N:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)[C:19]([O:21][C@@H:22]2[CH:27]3[CH2:28][CH2:29][N+:24]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:25][CH2:26]3)[CH2:23]2)=[O:20])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 107572-Chloroacetophenone2×HCID 86688942(R)-quinuclidin-3-yl 2-(4-fluorophenyl)-2-(piperidin-1-yl)acetate

Product 1

HCID 86688943(3R)-3-(2-(4-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chlorideYield 58.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (29.5 mg, 0.19 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(4-fluorophenyl)-2-(piperidin-1-yl)acetate (60 mg, 0.17 mmol) in EtOAc (3 ml). 2-Chloro-1-phenylethanone (8.85 mg, 0.06 mmol) were added and stirring was kept for 4 additional hours. Et2O was added and the precipitate was collected by suction filtration to obtain (3R)-3-(2-(4-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (49.9 mg, 57.5% yield) as a gummy yellow solid.

Workup

  1. filtrationthe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-3891752c0e184bdc80ae878cf780d4f4
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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