1,3-Difluorobenzene → 1-(Benzocyclobuten-1-ylmethyl)-4-(2,4-difluorobenzoyl)piperidine

HRID 2372744Notes

Reaction equation

HRID 2372744 reaction equation
[C:1]1([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16](Cl)=[O:17])[CH2:12][CH2:11]2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:2]=1.C(Cl)(=O)C(Cl)=O.[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[C:1]1([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16](=[O:17])[C:29]3[CH:30]=[CH:31][C:26]([F:25])=[CH:27][C:28]=3[F:32])[CH2:12][CH2:11]2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:2]=1

Participants

6

Reactant 4

HCID 97411,3-DifluorobenzeneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 198864251-(Benzocyclobuten-1-ylmethyl)-4-piperidinecarbonyl chloride

Product 1

HCID 198863571-(Benzocyclobuten-1-ylmethyl)-4-(2,4-difluorobenzoyl)piperidineYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.025 mole of 1-(benzocyclobuten-1-ylmethyl)-4-piperidinecarbonyl chloride (prepared by the action of oxalyl chloride on the acid described above), dissolved in 50 ml of dichloromethane, is introduced into a suspension of 0.025 mole of 1,3-difluorobenzene and 0.026 mole of aluminum trichloride in 10 ml of dichloromethane. When the gaseous evolution has ceased, the mixture is hydrolyzed with ice, settling is allowed to take place and the product is extracted with 1N hydrochloric acid. The aqueous phase is then alkalinized and extracted with dichloromethane. After evaporation of the solvent, the expected product is obtained.

Workup

  1. extractionthe product is extracted with 1N hydrochloric acid
  2. extractionextracted with dichloromethane
  3. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-76247e2f83e2441690e52fba6f27353e
Source dataset
uspto-grants-1992_03
Patent number
US05100902

Reaction notes

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