2-Chloroacetophenone → HCID 86672926, compound

HRID 1910491Notes

Reaction equation

HRID 1910491 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[N:11]12[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]1)[C@@H:13]([NH:19][C:20](=[O:35])[O:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12]2>C(OCC)(=O)C>[Cl-:1].[CH:22]([O:21][C:20]([NH:19][C@@H:13]1[CH:14]2[CH2:15][CH2:16][N+:11]([CH2:2][C:3](=[O:4])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)([CH2:18][CH2:17]2)[CH2:12]1)=[O:35])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 70675260HCID 70675260, compound

Product 1

HCID 86672926HCID 86672926, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (55.0 mg, 0.36 mmol) was added to a solution of (R)-benzhydryl quinuclidin-3-ylcarbamate (100 mg, 0.30 mmol, prepared as in example 2) in ethyl acetate (4 ml). The reaction was stirred at room temperature overnight. The suspension was decanted, solvent was removed, and the product was evaporated to dryness. Et2O was added, and the suspension was sonicated. The precipitate was collected by suction filtration and dried under vacuum at 40° C. to obtain (R)-3-(benzhydryloxycarbonylamino)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo-[2.2.2]octane chloride (110 mg)

Workup

  1. customThe suspension was decanted
  2. customsolvent was removed
  3. customthe product was evaporated to dryness
  4. additionEt2O was added
  5. customthe suspension was sonicated
  6. filtrationThe precipitate was collected by suction filtration
  7. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-d279ad35cff04b23be75e4d50191fda1
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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