Hydrochloric Acid → HCID 70873709, compound

HRID 2172237Notes

Reaction equation

HRID 2172237 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][C:24](OCC)([O:27]CC)[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86709389HCID 86709389, compound

Product 1

HCID 70873709HCID 70873709, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(4′-Benzyloxybiphenyl-4-yl)-4,4-diethoxy-piperidine (10.0 g, 23.2 mmol), acetone (100 ml) and a 5 N hydrochloric acid aqueous solution (35 ml) were mixed and heated under reflux for 5 hours. 1 N sodium hydroxide was added to the residue obtained by removing the solvent by distillation, followed by extraction with dichloromethane. The organic layer was washed with water and then dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The resulting crude crystal was washed with diethylether to afford the title compound as a white powder (7.2 g, yield 87%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. customobtained
  4. customby removing the solvent
  5. distillationby distillation
  6. extractionfollowed by extraction with dichloromethane
  7. washThe organic layer was washed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationAfter filtering
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. washThe resulting crude crystal was washed with diethylether

Sources & evidence

ORD record
ord-22787d3049824968a49dbdf8e95f7dde
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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