Potassium Hydroxide → 3543-21-3

HRID 2387952Notes

Reaction equation

HRID 2387952 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 of KOH were added to a solution of 7.3 g (1 equiv.) of benzyloxycarbonyl-4-phenyl-4-(pyrrolidin-1-yl)piperidine in 100 ml of ethanol, and the reaction mixture was heated for 24 hours at reflux. The progress of the reaction was monitored by thin-layer chromatography (20% MeOH/CHCl3). When the reaction was complete, the solvent was distilled off completely, 100 ml of water were added to the residue, and extraction was carried out 3× with 100 ml of CHCl3. The combined organic phases were dried with Na2SO4. After 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 heated for 24 hours
  2. temperatureat reflux
  3. distillationthe solvent was distilled off completely
  4. addition100 ml of water were added to the residue, and extraction
  5. dry with materialThe combined organic phases were dried with Na2SO4
  6. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-baa4d7cc115d45bdbacd158e022d9ddf
Source dataset
uspto-grants-2012_09
Patent number
US08269000B2

Reaction notes

Loading…