2-Chloroacetophenone → HCID 86688910, compound

HRID 404652Notes

Reaction equation

HRID 404652 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]([O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[O:12])[CH2:6][CH2:5]1)(=[O:3])[NH2:2].[Cl:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>CCOC(C)=O.C(#N)C>[Cl-:28].[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]([O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N+:16]([CH2:29][C:30](=[O:31])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([CH2:17][CH2:18]3)[CH2:15]2)=[O:12])[CH2:6][CH2:5]1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 107572-ChloroacetophenoneHCID 86688909HCID 86688909, compound

Product 1

HCID 86688910HCID 86688910, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-Quinuclidin-3-yl 2-(4-carbamoylpiperidin-1-yl)-2-phenylacetate (72 mg, 0.19 mmol) was dissolved in a mixture EtOAc (1.3 ml) and acetonitrile (0.6 ml). 2-Chloro-1-phenylethanone (33.0 mg, 0.21 mmol) was added and the mixture was reacted at the same temperature for three days. The mixture was evaporated and the crude was purified by flash chromatography (DCM/MeOH=85/15 to 8/2) to obtain (3R)-3-(2-(4-carbamoylpiperidin-1-yl)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (34 mg, 33.3% yield) as a pale yellow solid.

Workup

  1. customthe mixture was reacted at the same temperature for three days
  2. customThe mixture was evaporated
  3. customthe crude was purified by flash chromatography (DCM/MeOH=85/15 to 8/2)

Sources & evidence

ORD record
ord-9476b4a0ef6749ccacd4cea4329c65fa
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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