HCID 19390916, compound → HCID 19390930, compound

HRID 487176Notes

Reaction equation

HRID 487176 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16](O)[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 19390916HCID 19390916, compound

Product 1

HCID 19390930HCID 19390930, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

To an ethanolic solution (10 ml) of 0.3 g of the 1-benzyl-4-[3-hydroxy-3-(4-pyrrolidinophenyl)propyl]piperidine synthesized in Example 77 was added one drop of concentrated hydrochloric acid and the mixture was refluxed for 30 minutes. The solvent was then distilled off under reduced pressure and the residue was dissolved in dichloromethane. The solution was washed with water and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to give crude crystals. Recrystallization from hexane yielded 0.25 g of colorless crystals melting at 115°-117° C.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. distillationThe solvent was then distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto give crude crystals
  8. customRecrystallization from hexane

Sources & evidence

ORD record
ord-8bce66daa9d24f0d985250f3faff4136
Source dataset
uspto-grants-1994_03
Patent number
US05294625

Reaction notes

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