Hydrochloric Acid → HCID 18432004, compound

HRID 2305257Notes

Reaction equation

HRID 2305257 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](Cl)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCCl>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([C:23]2[CH:22]=[CH:21][C:20]([C:17]3[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=3)=[CH:25][CH:24]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 94614-FluorobiphenylHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18432004HCID 18432004, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

12.5 g of acetyl-4-piperidinecarbonyl chloride were added portionwise to a mixture of 10 g of 4-fluoro-1,1′-biphenyl, 17.5 g of aluminum-(III)-chloride and 60 g of 1,2-di-chloroethane. Upon completion, stirring was continued for 1 hour at reflux temperature. The reaction mixture was poured into a mixture of crushed ice and hydrochloric acid. The product was extracted with DCM. The extract was dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 15 g (80.8%) of 1-acetyl-4-[(4′-fluoro-[1,1′-biphenyl]-4-yl]carbonyl]piperidine (interm. 3).

Workup

  1. temperatureat reflux temperature
  2. extractionThe product was extracted with DCM
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 2-propanol
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-930383670b8a45adaccba25df3a959fa
Source dataset
uspto-grants-2002_08
Patent number
US06440440B1

Reaction notes

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