Potassium Iodide → HCID 86744214, compound

HRID 2051018Notes

Reaction equation

HRID 2051018 reaction equation
Cl.Cl[CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[CH2:12][CH2:13][CH2:14][CH2:15][C:8]2=[N:7][C:6]=1[CH3:16].Cl.Cl.[N:19]1([C:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[S:27][N:26]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[C:34](=[O:37])([O-:36])[O-].[Na+].[Na+].[I-].[K+].CC(C)CC(=[O:47])C>>[C:10]([OH:11])(=[O:47])/[CH:5]=[CH:6]/[C:34]([OH:36])=[O:37].[S:27]1[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:25]([N:19]2[CH2:20][CH2:21][N:22]([CH2:3][CH2:4][C:5]3[C:10](=[O:11])[N:9]4[CH2:12][CH2:13][CH2:14][CH2:15][C:8]4=[N:7][C:6]=3[CH3:16])[CH2:23][CH2:24]2)=[N:26]1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 156057823-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one--hydrogen chloride (1/1)HCID 19834477HCID 19834477, compound

Product 1

HCID 86744214HCID 86744214, compoundYield 85%

Procedure

A mixture of 5 parts of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one monohydrochloride, 5 parts of 3-(1-piperazinyl)-1,2-benzisothiazole dihydrochloride, 8 parts of sodium carbonate, 0.2 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone was stirred for 20 hours at reflux temperature. The reaction mixture was filtered and 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 converted into the (E)-2-butenedioate salt in 2-propanol. The salt was filtered off and crystallized from ethanol. The product was filtered off and dried, yielding 7.4 parts (85%) of 3-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (E)-2-butenedioate(1:1); mp. 186.0° C. (compound 1).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. filtrationThe salt was filtered off
  9. customcrystallized from ethanol
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-df1a50f8668c4fb5b0b2100d09a8b860
Source dataset
uspto-grants-1991_05
Patent number
US05015740

Reaction notes

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