2-(Chloroacetyl)thiophene → 4-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiophen-2-yl)ethyl)piperidinium chloride

HRID 1910516Notes

Reaction equation

HRID 1910516 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH:11]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[Cl:26][CH2:27][C:28]([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)=[O:29]>C(OCC)(=O)C>[Cl-:26].[F:25][C:21]1[CH:20]=[C:19]([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[O:10][C:8]([CH:5]2[CH2:4][CH2:3][N+:2]([CH3:1])([CH2:27][C:28](=[O:29])[C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[CH2:7][CH2:6]2)=[O:9])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 27579252-(Chloroacetyl)thiopheneHCID 70925814Bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate

Product 1

HCID 866729484-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiophen-2-yl)ethyl)piperidinium chlorideYield 8.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate (150 mg, 0.43 mmol) in ethyl acetate (5 ml), 2-chloro-1-(thiophen-2-yl)ethanone (69.8 mg, 0.43 mmol) was added, and the mixture was stirred at room temperature overnight. The solvent was removed under vacuum, and the residue was taken up in diethyl ether, filtered, and purified by flash chromatography (DCM/MeOH=95/5) to obtain 4-((bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiophen-2-yl)ethyl)piperidinium chloride (18 mg).

Workup

  1. customThe solvent was removed under vacuum
  2. filtrationfiltered
  3. custompurified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-82ccf430c1f24952a8f97554276f548e
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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