Hydrochloric Acid → HCID 23035196, compound

HRID 1710033Notes

Reaction equation

HRID 1710033 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH:10]=[N:9]2)[CH:5]=[C:4]([Cl:16])[C:3]=1[CH:17]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:18](Cl)=[O:19].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.Cl>O>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([CH:17]([C:3]2[C:4]([Cl:16])=[CH:5][C:6]([N:8]3[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH:10]=[N:9]3)=[CH:7][C:2]=2[Cl:1])[C:18]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:19])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 225573202,6-dichloro-alpha-(4-chlorophenyl)-4(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetylchloride

Product 1

HCID 23035196HCID 23035196, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.28 parts of 2,6-dichloro-α-(4-chlorophenyl)-4(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetylchloride and 18 parts of piperidine was stirred for 17 hours at room temperature (exothermic reaction). After the addition of water, the solution was acidified with hydrochloric acid. The product was extracted with a mixture of trichloromethane and methanol (95:5 by volume). The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and acetic acid (95:4:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was washed with 2,2'-oxybispropane and dried, yielding 1 part (44.0%) 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]piperidine; mp. 216.9° C. (intermediate 34).

Workup

  1. custom(exothermic reaction)
  2. extractionThe product was extracted with a mixture of trichloromethane and methanol (95:5 by volume)
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane, methanol and acetic acid (95:4:1 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. washThe residue was washed with 2,2'-oxybispropane
  11. customdried

Sources & evidence

ORD record
ord-1ebbaec060ab4f90827a521287601ea2
Source dataset
uspto-grants-1990_08
Patent number
US04952570

Reaction notes

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