2-Bromo-1-(thiophen-3-yl)ethan-1-one → 4-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiophen-3-yl)ethyl)piperidinium bromide

HRID 1910517Notes

Reaction equation

HRID 1910517 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)=[O:4].[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH:20]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=[O:18])[CH2:13][CH2:12]1>CCOC(C)=O>[Br-:1].[F:34][C:30]1[CH:29]=[C:28]([CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[O:19][C:17]([CH:14]2[CH2:13][CH2:12][N+:11]([CH3:10])([CH2:2][C:3](=[O:4])[C:5]3[CH:9]=[CH:8][S:7][CH:6]=3)[CH2:16][CH2:15]2)=[O:18])[CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-oneHCID 70925814Bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate

Product 1

HCID 866729504-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiophen-3-yl)ethyl)piperidinium bromideYield 54.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(thiophen-3-yl)ethanone (23.7 mg, 0.12 mmol) was added to a solution of bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate (40 mg, 0.12 mmol, prepared as in example 40) in EtOAc (3 ml). The reaction was stirred at room temperature overnight. The solvent was evaporated, and the crude was purified by preparative HPLC (eluent: CH3CN/H2O) to obtain 4-((bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiophen-3-yl)ethyl)piperidinium bromide (36.1 mg).

Workup

  1. customThe solvent was evaporated
  2. customthe crude was purified by preparative HPLC (eluent: CH3CN/H2O)

Sources & evidence

ORD record
ord-b024410d0e2e44739b78fe8e56360f5f
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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