1-Methylpiperazine → HCID 23035201, compound

HRID 1710035Notes

Reaction equation

HRID 1710035 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:14]=[C:13]([N:15]2[C:20](=[O:21])[NH:19][C:18](=[O:22])[CH:17]=[N:16]2)[CH:12]=[C:11]([Cl:23])[C:10]=1[CH:24]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:25](Cl)=[O:26]>O1CCCC1>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([CH:24]([C:10]2[C:9]([Cl:8])=[CH:14][C:13]([N:15]3[C:20](=[O:21])[NH:19][C:18](=[O:22])[CH:17]=[N:16]3)=[CH:12][C:11]=2[Cl:23])[C:25]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:26])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 225573202,6-dichloro-alpha-(4-chlorophenyl)-4(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetylchloride

Product 1

HCID 23035201HCID 23035201, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 10 parts of 1-methylpiperazine in 45 parts of tetrahydrofuran was added dropwise a solution of 6.7 parts of 2,6-dichloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetyl chloride in 45 parts of tetrahydrofuran during a period of 5 minutes. Upon complete addition, stirring was continued for 2 hours at room temperature. After evaporation in vacuo, 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 in vacuo. The residue was boiled in acetonitrile. After cooling, the precipitated product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 4.8 parts (62.8%) of 1-[2-(4-chlorophenyl)-2-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)phenyl]acetyl]-4-methylpiperazine: mp. 261.5° C. (intermediate 36).

Workup

  1. additionUpon complete addition
  2. customAfter evaporation in vacuo
  3. customthe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated in vacuo
  7. temperatureAfter cooling
  8. filtrationthe precipitated product was filtered off
  9. washwashed with 2,2'-oxybispropane
  10. customdried

Sources & evidence

ORD record
ord-fdc93d676ce746659d62ddcfadb24a3f
Source dataset
uspto-grants-1990_08
Patent number
US04952570

Reaction notes

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