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

HRID 241582Notes

Reaction equation

HRID 241582 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 36.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,3-difluorobenzene (6.7 g, 58.7 mmol) and ammonium chloride (13.3 g, 250 mmol) are added to 15 ml of dichloromethane and cooled to room temperature; thereto is drop-added 50 ml of dichloromethane wherein 1-acetyl-4-piperidinyl carboxylic acid chloride (9.8 g, 51.8 mmol) is dissolved. A reaction is carried out at reflux for 3 hours and the resulting mixture is poured into a mixture of ice and hydrochloric acid after completion of reaction. The mixture is extracted with dichloromethane (20 ml×3). The organic phase is separated, dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness to obtain 5.01 g of a product, with a yield of 36%.

Workup

  1. dissolutionis dissolved
  2. temperatureat reflux for 3 hours
  3. customafter completion of reaction
  4. extractionThe mixture is extracted with dichloromethane (20 ml×3)
  5. customThe organic phase is separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-d2b563d9ab184d28a30b20eba2851210
Source dataset
uspto-grants-2014_02
Patent number
US08653069B2

Reaction notes

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