2-Chloroacetophenone → HCID 70673624, compound

HRID 1910492Notes

Reaction equation

HRID 1910492 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:37])[O:21][CH:22]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH2:12]2>C(OCC)(=O)C>[Cl-:1].[F:36][C:33]1[CH:34]=[CH:35][C:30]([CH:22]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[O:21][C:20]([NH:19][C@@H:13]2[CH:14]3[CH2:17][CH2:18][N+:11]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:16][CH2:15]3)[CH2:12]2)=[O:37])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 107572-Chloroacetophenone2×HCID 70673880HCID 70673880, compound

Product 1

HCID 70673624HCID 70673624, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (13 mg, 0.09 mmol) was added to a solution of (R)-bis(4-fluorophenyl)methyl quinuclidin-3-ylcarbamate (32.0 mg, 0.09 mmol, prepared as in example 3) in ethyl acetate (2 ml). The reaction was stirred at room temperature overnight. Then more 2-chloro-1-phenylethanone (2.7 mg, 0.02 mmol) was added to the solution, and the reaction was stirred for additional 24 hours. The reaction was evaporated to dryness, and the residue was triturated in Et2O. Then isopropyl ether was added, and the product was sonicated and the precipitate was collected by suction filtration to obtain (R)-3-((bis(4-fluorophenyl)methoxy)carbonylamino)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (32.4 mg)

Workup

  1. stirringthe reaction was stirred for additional 24 hours
  2. customThe reaction was evaporated to dryness
  3. customthe residue was triturated in Et2O
  4. additionThen isopropyl ether was added
  5. customthe product was sonicated
  6. filtrationthe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-4be59539d9c945208e5e1978860d9095
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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