2-Chloroacetophenone → HCID 86688924, compound

HRID 404663Notes

Reaction equation

HRID 404663 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]([O:10][C@@H:11]1[CH:16]2[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]2)[CH2:12]1)=[O:9].[Cl:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28].CCOCC.C(Cl)Cl>C(OCC)(=O)C.C(#N)C>[Cl-:25].[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]([O:10][C@@H:11]1[CH:16]2[CH2:15][CH2:14][N+:13]([CH2:26][C:27](=[O:28])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([CH2:18][CH2:17]2)[CH2:12]1)=[O:9]

Participants

6

Reactant 3

HCID 107572-ChloroacetophenoneHCID 21881112Ethyl ether methylene chlorideHCID 86688922HCID 86688922, compound

Product 1

HCID 86688924HCID 86688924, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-Quinuclidin-3-yl 2-((R)-2-methylpyrrolidin-1-yl)-2-phenylacetate (24c) (44 mg, 0.13 mmol) was dissolved in a mixture ethyl acetate (0.9 ml) and acetonitrile (0.4 ml). 2-Chloro-1-phenylethanone (22.8 mg, 0.15 mmol) was added and the mixture was stirred at room temperature for 48 hours. The solution was evaporated and the residue was purified first by flash chromatography (DCM/MeOH=90/10 to 85/15) and then by trituration with Et2O/DCM (about 5/1) to obtain the title compound (23 mg, 35.5% yield) as a pale yellow solid.

Workup

  1. customThe solution was evaporated
  2. customthe residue was purified first by flash chromatography (DCM/MeOH=90/10 to 85/15)

Sources & evidence

ORD record
ord-aeb43fda227e4ab2848e068e2939eac5
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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