Hydrochloric Acid → 1-Acetyl-4-(2',4'-difluorobenzoyl)piperidine

HRID 1270666Notes

Reaction equation

HRID 1270666 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.[Cl-].[NH4+].[C:11]([N:14]1[CH2:19][CH2:18][CH:17]([C:20](Cl)=[O:21])[CH2:16][CH2:15]1)(=[O:13])[CH3:12].Cl>ClCCl>[C:11]([N:14]1[CH2:15][CH2:16][CH:17]([C:20](=[O:21])[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[F:8])[CH2:18][CH2:19]1)(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97411,3-DifluorobenzeneHCID 25517Ammonium ChlorideHCID 1009501-Acetylpiperidine-4-carbonyl chloride

Product 1

HCID 27407071-Acetyl-4-(2',4'-difluorobenzoyl)piperidineYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

67 g of 1,3-difluorobenzene and 133 g of ammonium chloride were added to 150 ml of dichloromethane, and then the mixture was cooled to room temperature. 98 g of 1-acetyl-4-piperidinecarbonyl chloride in 50 ml of dichloromethane was added thereto dropwise, and then the mixture was stirred at an elevated temperature for 3 hours. The reaction mixture was poured to a mixture of ice and hydrochloric acid, and the resulting mixture was extracted with 200 ml of dichloromethane. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate to obtain 55.9 g of the title compound (yield: 41%).

Workup

  1. extractionthe resulting mixture was extracted with 200 ml of dichloromethane
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed from the filtrate

Sources & evidence

ORD record
ord-8f5e55c335594cdb9da2e72c9b389815
Source dataset
uspto-grants-2007_04
Patent number
US07202360B2

Reaction notes

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