Potassium Iodide → HCID 23326063, compound

HRID 484737Notes

Reaction equation

HRID 484737 reaction equation
[ClH:1].[Cl:2][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.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:21][CH:20]=1.C[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)CC(=O)C>[ClH:2].[ClH:1].[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[C:26]2[CH2:27][CH2:28][N:29]([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])[CH2:30][CH2:31]2)=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 10942334Sodium MethoxideHCID 156057823-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one--hydrogen chloride (1/1)HCID 70401247HCID 70401247, compound

Product 1

HCID 23326063HCID 23326063, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.5 parts of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride, 4.6 parts of 4-[(4-fluorophenyl)phenylmethylene]piperidine hydrochloride, 2 parts of a sodium methoxide solution 30%, 8 parts of sodium carbonate, 0.2 parts of potassium iodide and 240 parts of 4-methyl-2-pentanone was stirred and refluxed for 22 hours. The reaction mixture was filtered hot and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (92:8 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in acetonitrile and 2-propanol. The salt was filtered off and dried, yielding 4.8 parts (60%) of 3-[2-[4-[(4-fluorophenyl)phenylmethylene]-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one dihydrochloride; mp. 264.6° C. (compound 137).

Workup

  1. temperaturerefluxed for 22 hours
  2. filtrationThe reaction mixture was filtered hot
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (92:8 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. filtrationThe salt was filtered off
  9. customdried

Sources & evidence

ORD record
ord-6d038c3ee6cc4d00b44d76dbcedcad9e
Source dataset
uspto-grants-1985_08
Patent number
US04533665

Reaction notes

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