Potassium Iodide → 3-[2-(4-benzoyl-1-piperidinyl)ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 66685Notes

Reaction equation

HRID 66685 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].Br.[C:17]1([C:23]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[C:23]([CH:25]1[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][C:4]2[C:9](=[O:10])[N:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]3=[N:6][C:5]=2[CH3:15])[CH2:27][CH2:26]1)(=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 8178663-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 20530718Phenyl(piperidin-4-yl)methanone hydrobromide

Product 1

HCID 130359103-[2-(4-benzoyl-1-piperidinyl)ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5.6 parts of 3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 6 parts of phenyl(4-piperidinyl)-methanone hydrobromide, 8 parts of sodium carbonate, 0.1 parts of potassium iodide and 240 parts of 4-methyl-2-pentanone is stirred and refluxed for 24 hours using a water-separator. The reaction mixture is filtered hot over Hyflo and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 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 6 parts of 3-[2-(4-benzoyl-1-piperidinyl)ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 122.2° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. filtrationThe reaction mixture is filtered hot over Hyflo
  3. customthe filtrate is evaporated
  4. customThe residue is purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (90:10 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

Sources & evidence

ORD record
ord-f8d6d80ba41a4864a815f3d5a9a3c597
Source dataset
uspto-grants-1982_08
Patent number
US04342870

Reaction notes

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