Potassium Iodide → HCID 15586425, compound

HRID 371101Notes

Reaction equation

HRID 371101 reaction equation
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[C:11]([CH3:14])=[CH:12][S:13][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+].[I-].[K+]>O.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[C:11]([CH3:14])=[CH:12][S:13][C:7]4=[N:6][C:5]=3[CH3:15])[CH2:28][CH2:27]2)=[O:25])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 134778116-(2-Chloroethyl)-3,7-dimethyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 15586425HCID 15586425, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.75 parts of 6-(2-chloroethyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5 -one, 3.6 parts of (4-fluorophenyl) (4-piperidinyl)methanone hydrochloride, 12 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone was stirred and refluxed for 22 hours using a water-separator. The reaction mixture was filtered hot over Hyflo and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane, yielding 5 parts of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one; mp. 199.7° C. (compound 4).

Workup

  1. temperaturerefluxed for 22 hours
  2. filtrationThe reaction mixture was filtered hot over Hyflo
  3. customthe filtrate was evaporated
  4. customThe residue was 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 were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-97ebd1e2daac40dfb5ce0a2d62147145
Source dataset
uspto-grants-1985_07
Patent number
US04529727

Reaction notes

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