2-Chloroacetophenone → HCID 86660338, compound

HRID 469507Notes

Reaction equation

HRID 469507 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH2:11]([C:13]1[CH:14]=[C:15]([NH:19][CH:20]([C:32]2[CH:33]=[N:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)[C:21]([O:23][C@@H:24]2[CH:29]3[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]3)[CH2:25]2)=[O:22])[CH:16]=[CH:17][CH:18]=1)[CH3:12]>CCOC(C)=O>[Cl-:1].[CH2:11]([C:13]1[CH:14]=[C:15]([NH:19][CH:20]([C:32]2[CH:33]=[N:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)[C:21]([O:23][C@@H:24]2[CH:29]3[CH2:28][CH2:27][N+:26]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:31][CH2:30]3)[CH2:25]2)=[O:22])[CH:16]=[CH:17][CH:18]=1)[CH3:12]

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 58556995HCID 58556995, compound

Product 1

HCID 86660338HCID 86660338, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (143 mg, 0.93 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(3-ethylphenylamino)-2-(6-methoxypyridin-3-yl)acetate (C74) (366 mg, 0.93 mmol) in EtOAc (3 ml), and the resulting reaction was stirred at room temperature overnight. The solvent was evaporated, and the crude product was purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(3-ethylphenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (69.3 mg, 13.6% yield over two steps).

Workup

  1. customthe resulting reaction
  2. customThe solvent was evaporated
  3. customthe crude product was purified by preparative HPLC (Eluent: CH3CN/H2O)

Sources & evidence

ORD record
ord-71d3ac9e30bb4ccfa5374e83e9fe143f
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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