Phenacyl bromide → HCID 86688889, compound

HRID 404628Notes

Reaction equation

HRID 404628 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH: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])[CH2:4][CH2:3]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].[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 86688888HCID 86688888, compound

Product 1

HCID 86688889HCID 86688889, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-Quinuclidin-3-yl 2-(4-methylpiperidin-1-yl)-2-phenylacetate (58 mg, 0.17 mmol) and 2-bromo-1-phenylethanone (37.1 mg, 0.19 mmol) were dissolved in acetonitrile (3 ml) and stirred at room temperature overnight. The solvent was evaporated and the residue was tritured with Et2O and filtered under vacuum. The recovered solid was further purified by preparative HPLC to obtain (3R)-3-(2-(4-methylpiperidin-1-yl)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (5 mg, 5.5% yield) as a colorless oil.

Workup

  1. customThe solvent was evaporated
  2. filtrationfiltered under vacuum
  3. customThe recovered solid was further purified by preparative HPLC

Sources & evidence

ORD record
ord-bbf1caa97f5f48789df429c09b09bfe2
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

Loading…