Hydrochloric Acid → 4-[5,5-Bis(4-fluorophenyl)-4-pentenyl]-2-piperazinecarboxamide monohydrate

HRID 1638612Notes

Reaction equation

HRID 1638612 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]3C(C)(C)[NH:20][C:21](=[O:22])[CH:15]3[CH2:14]2)=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>>[OH2:22].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[CH:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH:15]([C:21]([NH2:20])=[O:22])[CH2:14]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 147225477-[5,5-bis(4-fluorophenyl)-4-pentenyl]hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-one

Product 1

HCID 221580484-[5,5-Bis(4-fluorophenyl)-4-pentenyl]-2-piperazinecarboxamide monohydrateYield 50%

Procedure

A mixture of 60 parts of 7-[5,5-bis(4-fluorophenyl)-4-pentenyl]hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-one and 850 parts of a hydrochloric acid solution 0.5N was stirred for 2 hours at reflux temperature. After cooling, the reaction mixture was treated with potassium carbonate. The product was extracted with trichloromethane. The extract was dried, filtered and 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 1,1'-oxybisethane. The product was filtered off and dried, yielding 29.5 parts (50%) of 4-[5,5-bis(4-fluorophenyl)-4-pentenyl]-2-piperazinecarboxamide monohydrate; mp. 51.3° C. (int. 25).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. extractionThe product was extracted with trichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from 1,1'-oxybisethane
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-0bb726c66f0b412db2049b9fb967ff91
Source dataset
uspto-grants-1989_11
Patent number
US04880808

Reaction notes

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