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

HRID 654750Notes

Reaction equation

HRID 654750 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 1 N 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 1 N hydrochloric acid
  2. extractionextracted with dichloromethane
  3. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-070eda3ef6614cc88a2bd1ec02c1a5ad
Source dataset
uspto-grants-1992_07
Patent number
US05134147

Reaction notes

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