4-(4-Fluorobenzoyl)piperidine → HCID 15096985, compound

HRID 345582Notes

Reaction equation

HRID 345582 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.Cl[CH2:17][CH2:18][NH:19][C:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)=[O:21]>CC(C)CC(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:17][CH2:18][NH:19][C:20]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[O:21])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 10535514N-(2-Chloroethyl)-3-pyridinecarboxamide

Product 1

HCID 15096985HCID 15096985, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a stirred solution of 11.2 parts of (4-fluorophenyl)(4-piperidinyl)methanone in 80 parts of 4-methyl-2-pentanone were added 5 parts of N-(2-chloroethyl)-3-pyridinecarboxamide and the whole was stirred and refluxed overnight. The reaction mixture was filtered and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane, yielding 1.6 parts (16.5%) of N-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-3-pyridinecarboxamide; mp. 118.3° C. (intermediate 114).

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-4b938e8867404167ad7bc8d1c29505c6
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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