2-Chloroacetophenone → HCID 86660324, compound

HRID 469466Notes

Reaction equation

HRID 469466 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]([C@@H:16]([NH:28][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:35]=[CH:36][CH:37]=[CH:38][C:12]1=2>CC#N>[Cl-:1].[S:11]1[CH:15]=[C:14]([C@@H:16]([NH:28][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:35]=[CH:36][CH:37]=[CH:38][C:12]1=2

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 58556993HCID 58556993, compound

Product 1

HCID 86660324HCID 86660324, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-1-phenylethanone (98 mg, 0.64 mmol) was added to a solution of (R)—((R)-quinuclidin-3-yl) 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate (diastereomer 1 of C19) (250 mg, 0.64 mmol) in CH3CN (3 ml). The reaction mixture was stirred at r.t. overnight, and then the solvent was evaporated and the residue was triturated with Et2O. The crude was purified by preparative HPLC (Eluent: CH3CN/H2O), to obtain (R)-3-((R)-2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (210 mg, 60.3% yield).

Workup

  1. customthe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. customThe crude was purified by preparative HPLC (Eluent: CH3CN/H2O)

Sources & evidence

ORD record
ord-97d2c20820644ebbb3955aaeb869dd1d
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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