Sodium Carbonate → Pirenperone

HRID 66684Notes

Reaction equation

HRID 66684 reaction equation
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]2=[N:6][C:5]=1[CH3:15].Cl.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]([CH:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][C:4]3[C:9](=[O:10])[N:8]4[CH:11]=[CH:12][CH:13]=[CH:14][C:7]4=[N:6][C:5]=3[CH3:15])[CH2:28][CH2:27]2)=[O:25])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 8178663-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 4847Pirenperone

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5 parts of 3-(2-chloroethyl)-2-methyl-4H-pyrido-[1,2-a]pyrimidin-4-one, 4.9 parts of (4-fluorophenyl)(4-piperidinyl)-methanone hydrochloride, 5 parts of sodium carbonate and 160 parts of 4-methyl-2-pentanone is stirred and refluxed for 24 hours. The reaction mixture is cooled, washed with water and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (92:8 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, yielding 3 parts of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 139° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureThe reaction mixture is cooled
  3. washwashed with water
  4. customthe layers are separated
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (92:8 by volume) as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. customThe residue is crystallized from a mixture of ethanol and 1,1'-oxybisethane

Sources & evidence

ORD record
ord-39c0fd0ff4d143569e5d314689db5cef
Source dataset
uspto-grants-1982_08
Patent number
US04342870

Reaction notes

Loading…