Potassium Iodide → 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-phenyl-4(3H)-quinazolinone

HRID 1156356Notes

Reaction equation

HRID 1156356 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.[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)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]([CH:31]2[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][N:4]3[C:13](=[O:14])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[N:6]=[C:5]3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:33][CH2:32]2)=[O:30])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 27720803-(2-chloroethyl)-2-phenylquinazolin-4(3H)-oneHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 128520683-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-phenyl-4(3H)-quinazolinoneYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5.5 parts of 3-(2-chloroethyl)-2-phenyl-4(3H)-quinazolinone, 4 parts of (4-fluorophenyl)(4-piperidinyl)methanone hydrochloride, 7 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 24 hours using a water-separator. The reaction mixture is filtered while hot. The filtrate 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 residue is crystallized from a mixture of ethanol and 1,1'-oxybisethane. The product is filtered off and dried, yielding 5 parts (69%) of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-phenyl-4(3H)-quinazolinone; mp. 143.8° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. filtrationThe reaction mixture is filtered while hot
  3. customThe filtrate is evaporated
  4. customThe residue is 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 are collected
  7. customthe eluent is evaporated
  8. customThe residue is crystallized from a mixture of ethanol and 1,1'-oxybisethane
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-17c64b0d61264e1a84fd3c2b86ae4b03
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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