Hydrochloric Acid → 4-(Diphenylmethoxy)piperidinium chloride

HRID 465016Notes

Reaction equation

HRID 465016 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([O:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[K+].[ClH:28]>C(O)(C)C>[ClH:28].[C:20]1([CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:12][CH:9]2[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10020094Ethyl 4-(diphenylmethoxy)piperidine carboxylate

Product 1

HCID 441535184-(Diphenylmethoxy)piperidinium chlorideYield 71%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1-ethoxycarbonyl-4-diphenylmethoxypiperidine (60 g; 0.176 moles) and 85% potassium hydroxide (116 g; 1.76 moles) in isopropanol (600 ml) was boiled under reflux for 6 hours. After cooling, concentrated hydrochloric acid was added until pH=2 and the solvent removed in vacuo. The resulting residue was dissolved in a small quantity of water, washed with diethyl ether and the aqueous solution was made alkaline with aqueous sodium hydroxide solution and extracted with methylene chloride. The organic solution was dried (Na2SO4), the solvent removed in vacuo and the residual oil treated with ethanolic hydrogen chloride solution. 4-Diphenylmethoxy-piperidine hydrochloride (38 g; yield 71%) was obtained.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureAfter cooling
  3. customthe solvent removed in vacuo
  4. dissolutionThe resulting residue was dissolved in a small quantity of water
  5. washwashed with diethyl ether
  6. extractionextracted with methylene chloride
  7. dry with materialThe organic solution was dried (Na2SO4)
  8. customthe solvent removed in vacuo
  9. additionthe residual oil treated with ethanolic hydrogen chloride solution

Sources & evidence

ORD record
ord-dcb4d11fa0a54c4a8e3b922719fc5c8c
Source dataset
uspto-grants-1985_10
Patent number
US04550116

Reaction notes

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