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Acetyl chloride → 1-[4-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidino]-1-ethanone

HRID 748805
Notes
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Reaction equation

HRID 748805 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34].C(=O)(O)[O-].[Na+]>ClCCl.CCCCCC>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[CH2:17][CH2:16][N:15]([C:33](=[O:35])[CH3:34])[CH2:14][CH2:13]2)(=[O:10])=[O:11])=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 692029464-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidine Hydrochloride

Product 1

HCID 597507641-[4-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidino]-1-ethanoneYield 54.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

The 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidine hydrochloride (90 mg, 0.22 mmol) obtained in Example 260 and triethylamine (0.092 ml, 0.66 mmol) were dissolved in dichloromethane (4 ml), followed by the addition of acetyl chloride (0.024 ml, 0.34 mmol) at room temperature. After stirring at room temperature for 14 hours, a saturated aqueous solution of sodium bicarbonate (0.5 ml) was added. The residue obtained by concentrating the resulting mixture under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the dichloromethane:methanol=30:1 eluate was concentrated under reduced pressure to give a white solid. The solid thus obtained was washed with hexane, whereby the title compound (48 mg, 0.12 mmol, 53%) was obtained as a white powder.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the resulting mixture under reduced pressure
  3. customthe fraction obtained from the dichloromethane
  4. concentrationmethanol=30:1 eluate was concentrated under reduced pressure
  5. customto give a white solid
  6. customThe solid thus obtained

Sources & evidence

ORD record
ord-da07564f89474b73b7a818b99b0e27e2
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07399775B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes