Phenacyl bromide → HCID 86688914, compound

HRID 404655Notes

Reaction equation

HRID 404655 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][N:4]([CH:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]([O:12][C@@H:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[O:11])[CH2:3]1.[Br:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30]>C(#N)C>[Br-:27].[CH3:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][N:4]([CH:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]([O:12][C@@H:13]2[CH:18]3[CH2:17][CH2:16][N+:15]([CH2:28][C:29](=[O:30])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)([CH2:20][CH2:19]3)[CH2:14]2)=[O:11])[CH2:3]1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 86688913HCID 86688913, compound

Product 1

HCID 86688914HCID 86688914, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-quinuclidin-3-yl 2-(3,5-dimethylpiperidin-1-yl)-2-phenylacetate (120 mg, 0.34 mmol) and 2-bromo-1-phenylethanone (73.7 mg, 0.37 mmol) were dissolved in acetonitrile (5 ml) and stirred at room temperature for 16 hours. Acetonitrile was evaporated, the residue was taken up with little EtOAc (2 ml) and then Et2O was added. The white solid that precipitated out was recovered by suction filtration and washed on the filter paper with Et2O. The solid was dried to obtain (3R)-3-(2-(3,5-dimethylpiperidin-1-yl)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (115.8 mg, 61.9% yield).

Workup

  1. customAcetonitrile was evaporated
  2. additionEt2O was added
  3. customThe white solid that precipitated out
  4. filtrationwas recovered by suction filtration
  5. washwashed on the filter paper with Et2O
  6. customThe solid was dried

Sources & evidence

ORD record
ord-82e1b2dacb1e4a92bd56dd825da16b40
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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