2-Chloroacetophenone → (3R)-3-(2-(benzo[b]thiophen-3-yl)-2-(methyl(phenyl)amino)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 469477Notes

Reaction equation

HRID 469477 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[S:11]1[CH:15]=[C:14]([CH:16]([N:28]([CH3:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:17]([O:19][C@@H:20]2[CH:25]3[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]3)[CH2:21]2)=[O:18])[C:13]2[CH:36]=[CH:37][CH:38]=[CH:39][C:12]1=2>C(#N)C>[Cl-:1].[S:11]1[CH:15]=[C:14]([CH:16]([N:28]([CH3:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:17]([O:19][C@@H:20]2[CH:25]3[CH2:26][CH2:27][N+:22]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:23][CH2:24]3)[CH2:21]2)=[O:18])[C:13]2[CH:36]=[CH:37][CH:38]=[CH:39][C:12]1=2

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 58556999(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(methyl(phenyl)amino)acetate

Product 1

HCID 86660329(3R)-3-(2-(benzo[b]thiophen-3-yl)-2-(methyl(phenyl)amino)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chlorideYield 74.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-1-phenylethanone (42.6 mg, 0.27 mmol) was added to solution of (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(methyl(phenyl)amino)acetate (C35) (112 mg, 0.27 mmol) in acetonitrile (3 ml). The reaction was stirred at room temperature for 3 hours, and then the solvent was evaporated under vacuum. The residue was triturated with Et2O, filtered and dried to obtain (3R)-3-(2-(benzo[b]thiophen-3-yl)-2-(methyl(phenyl)amino)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (112.2 mg, 72.6% yield).

Workup

  1. customthe solvent was evaporated under vacuum
  2. customThe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-6899f4f70800499cb156b2ae7603928c
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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