Sodium Hydroxide → 4-Benzhydryloxypiperidine

HRID 2297512Notes

Reaction equation

HRID 2297512 reaction equation
[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12](C(OCC)=O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C.O>[C:20]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10020094Ethyl 4-(diphenylmethoxy)piperidine carboxylate

Product 1

HCID 30175844-BenzhydryloxypiperidineYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 4-(diphenylmethoxy)piperidine carboxylate (9.7 g) was dissolved in ethanol (85 ml) and water (35 ml), and sodium hydroxide (6.1 g) was added to the mixture, followed by heating the mixture to reflux for 40 hours. Ethanol was removed and water was added to the residue, followed by extraction of the resultant with dichloromethane. Organic layers were combined and dried over anhydrous sodium sulfate. Dichloromethane was removed and the residue was purified with Chromatorex® column chromatography for amines (ethyl acetate:ethanol=5:1) to obtain 7.1 of 4-diphenylmethoxypiperidine. Yield: 90%.

Workup

  1. temperatureby heating the mixture
  2. temperatureto reflux for 40 hours
  3. customEthanol was removed
  4. additionwater was added to the residue
  5. extractionfollowed by extraction of the resultant with dichloromethane
  6. dry with materialdried over anhydrous sodium sulfate
  7. customDichloromethane was removed
  8. customthe residue was purified with Chromatorex® column chromatography for amines (ethyl acetate:ethanol=5:1)

Sources & evidence

ORD record
ord-2d1493da9fdb4f5aa7d9c0dc638c99b4
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

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