4-(4-Fluorobenzoyl)piperidine → HCID 12852062, compound

HRID 1156353Notes

Reaction equation

HRID 1156353 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH2:13][CH2:14]Cl)[CH:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[O:30])=[CH:25][CH:24]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH2:13][CH2:14][N:34]1[CH2:35][CH2:36][CH:31]([C:29](=[O:30])[C:26]3[CH:25]=[CH:24][C:23]([F:22])=[CH:28][CH:27]=3)[CH2:32][CH2:33]1)[CH:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 20278944HCID 20278944, compound

Product 1

HCID 12852062HCID 12852062, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.8 parts of 6-chloro-3-(2-chloroethyl)-3,4-dihydro-4-phenyl-2(1H)-quinazolinone, 7.4 parts of (4-fluorophenyl) (4-piperidinyl)methanone and 56 parts of ethanol is stirred and refluxed overnight. The reaction mixture is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue solidifies on triturating in 2,2'-oxybispropane. The product is filtered off and dried, yielding 5 parts (57%) of 6-chloro-3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-3,4-dihydro-4-phenyl-2(1H)-quinazolinone; mp. 196° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. customThe residue is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. customon triturating in 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-b300dee5838d49aa976d8a871f94caf4
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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