Hydrochloric Acid → 4-[4,4-Bis(4-fluorophenyl)butyl]-2-piperazinemethanol

HRID 35331Notes

Reaction equation

HRID 35331 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]3C(C)(C)[O:19][CH2:20][CH:14]3[CH2:13]2)=[CH:4][CH:3]=1.Cl>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH:14]([CH2:20][OH:19])[CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 212957107-[4,4-bis(4-fluorophenyl)butyl]hexahydro-3,3-dimethyl-1H-oxazolo[3,4-a]pyrazine

Product 1

HCID 212956744-[4,4-Bis(4-fluorophenyl)butyl]-2-piperazinemethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 34 parts of 7-[4,4-bis(4-fluorophenyl)butyl]hexahydro-3,3-dimethyl-1H-oxazolo[3,4-a]pyrazine and 272 parts of a hydrochloric acid solution 0.5N in water was stirred and refluxed for 2 hours. The reaction mixture was cooled to room temperature and the product was extracted twice with 1,1'-oxybisethane. The aqueous phase was separated, alkalized and salted out with sodium 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 (85:15 by volume), saturated with ammonia as eluent. The pure fractions were collected and the eluent was evaporated, yielding 17.0 parts of 4-[4,4-bis(4-fluorophenyl)butyl]-2-piperazinemethanol as an oily residue (intermediate 100).

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionthe product was extracted twice with 1,1'-oxybisethane
  3. customThe aqueous phase was separated
  4. extractionThe product was extracted with trichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (85:15 by volume)
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-d0945cbf0d6f4484adc377c2d8f76bb2
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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