HCID 23137711, compound → HCID 23137703, compound

HRID 1436894Notes

Reaction equation

HRID 1436894 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C:14]([O:19][CH3:20])([O:17][CH3:18])[CH2:13][CH:12]1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[CH3:28])=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH:12]2[CH2:13][C:14]([O:19][CH3:20])([O:17][CH3:18])[CH2:15][CH2:16][NH:11]2)=[C:22]([CH3:28])[CH:23]=1

Participants

4

Reactant 1

HCID 23137711HCID 23137711, compound

Product 1

HCID 23137703HCID 23137703, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 300 ml of ethanol were added 30 g of 1-benzyloxycarbonyl-2-(4-fluoro-2-methylphenyl)-4,4-dimethoxypiperidine and 3.0 g of 10% palladium-carbon, and the mixture was stirred under hydrogen atmosphere at room temperature for 3 hours. From the reaction mixture was removed insoluble matters by filtration, and the solvent was removed by distillation under reduced pressure. To the residue was added 300 ml of ethyl acetate. Under ice-cooling 20 ml of 4M hydrochloric acid-ethyl acetate solution was slowly added dropwise. The crystals were collected by filtration and washed with ethyl acetate. After drying, the crystals were added to a mixture of dichloromethane—an aqueous sodium carbonate solution, and the mixture was stirred. After the organic layer was separated, the aqueous layer was further extracted with dichloromethane. The organic layers were combined and dried over sodium sulfate, the solvent was removed by distillation under reduced pressure, to give 16.7 g of 2-(4-fluoro-2-methylphenyl)-4,4-dimethoxypiperidine as shown in Table 125 below.

Workup

  1. customFrom the reaction mixture was removed insoluble matters
  2. filtrationby filtration
  3. customthe solvent was removed by distillation under reduced pressure
  4. additionTo the residue was added 300 ml of ethyl acetate
  5. temperatureUnder ice-cooling 20 ml of 4M hydrochloric acid-ethyl acetate solution
  6. additionwas slowly added dropwise
  7. filtrationThe crystals were collected by filtration
  8. washwashed with ethyl acetate
  9. customAfter drying
  10. additionthe crystals were added to a mixture of dichloromethane—an aqueous sodium carbonate solution
  11. stirringthe mixture was stirred
  12. customAfter the organic layer was separated
  13. extractionthe aqueous layer was further extracted with dichloromethane
  14. dry with materialdried over sodium sulfate
  15. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-83650859475a4a50a2f5b6d5194ce22e
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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