Potassium Hydroxide → 3543-21-3

HRID 1500321Notes

Reaction equation

HRID 1500321 reaction equation
[OH-].[K+].C(OC([N:13]1[CH2:18][CH2:17][C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1)=O)C1C=CC=CC=1.CO.C(Cl)(Cl)Cl>C(O)C>[C:24]1([C:16]2([N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[CH2:15][CH2:14][NH:13][CH2:18][CH2:17]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21584188Chloroform methanolHCID 67366133HCID 67366133, compound

Product 1

HCID 594016893543-21-3Yield 151.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11 g KOH were added to a solution of 7.3 g (1 eq) benzyloxycarbonyl-4-phenyl-4-(pyrrolidin-1-yl)piperidine in 100 ml ethanol and the reaction mixture was refluxed for 24 h. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). Once the conversion was complete, the solvent was distilled off completely and the residue mixed with 100 ml water and extracted 3 times with 100 ml CHCl3. The combined organic phases were dried with Na2SO4. Following removal of the solvent under reduced pressure, 7 g of crude product were obtained in the form of an oil.

Workup

  1. temperaturethe reaction mixture was refluxed for 24 h
  2. distillationthe solvent was distilled off completely
  3. additionthe residue mixed with 100 ml water
  4. extractionextracted 3 times with 100 ml CHCl3
  5. dry with materialThe combined organic phases were dried with Na2SO4
  6. customremoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-011bf44ee23a48e284d50fa83b8efb66
Source dataset
uspto-grants-2015_12
Patent number
US09206156B2

Reaction notes

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