Ethanol → HCID 12852061, compound

HRID 1156352Notes

Reaction equation

HRID 1156352 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:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]1=[O:21].[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>CN(C)C=O>[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:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:5]3=[O:21])[CH2:33][CH2:32]2)=[O:30])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 20278961HCID 20278961, compound

Product 1

HCID 12852061HCID 12852061, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6 parts of 3-(2-chloroethyl)-1-phenyl-2,4(1H,3H)-quinazolinedione, 8.3 parts of (4-fluorophenyl) (4-piperidinyl)methanone and 48 parts of ethanol is stirred and refluxed. N,N-dimethylformamide is added at reflux temperature till all solid enters solution. Stirring is continued overnight at reflux. The reaction mixture is evaporated. The residue is purified twice by column-chromatography over silica gel using first a mixture of trichloromethane and methanol (95:5 by volume) and then a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2-propanol, yielding 2.2 parts (23%) of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-1-phenyl-2,4(1H,3H)-quinazolinedione; mp. 166.1° C.

Workup

  1. temperaturerefluxed
  2. temperatureat reflux temperature till all solid
  3. stirringStirring
  4. temperatureat reflux
  5. customThe reaction mixture is evaporated
  6. customThe residue is purified twice by column-chromatography over silica gel using first
  7. additiona mixture of trichloromethane and methanol (95:5 by volume)
  8. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-2d6f0c66f09a46aba864ee25c5d13476
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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