Methyl Isobutyl Ketone → Setoperone

HRID 371100Notes

Reaction equation

HRID 371100 reaction equation
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][S:13][C:7]2=[N:6][C:5]=1[CH3:14].Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([CH:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][C:4]3[C:9](=[O:10])[N:8]4[CH2:11][CH2:12][S:13][C:7]4=[N:6][C:5]=3[CH3:14])[CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 15586423HCID 15586423, compound

Product 1

HCID 68604Setoperone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.3 parts of 6-(2-chloroethyl)-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, 3 parts of (4-fluorophenyl) (4-piperidinyl)methanone hydrochloride, 8 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone was stirred and refluxed for 20 hours using a water-separator. The reaction mixture was filtered hot over Hyflo and the filter-cake was washed with trichloromethane. The filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 2,2'-oxybispropane, yielding 2 parts of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one; mp. 165.6° C. (compound 1).

Workup

  1. temperaturerefluxed for 20 hours
  2. filtrationThe reaction mixture was filtered hot over Hyflo
  3. washthe filter-cake was washed with trichloromethane
  4. customThe filtrate was evaporated
  5. customThe residue was purified by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from a mixture of 2-propanone and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-d42c2ab6cd8f4522b914cc90fb31197a
Source dataset
uspto-grants-1985_07
Patent number
US04529727

Reaction notes

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