Diethyl Ether → 1-[[[4-(Phenylmethyl)-1-piperazinyl]carbonyl]amino]cyclohexanecarboxylic acid

HRID 1627449Notes

Reaction equation

HRID 1627449 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1([NH:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])C.CCOCC>C(O)C>[C:24]1([CH2:23][N:20]2[CH2:19][CH2:18][N:17]([C:15]([NH:14][C:8]3([C:6]([OH:7])=[O:5])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:16])[CH2:22][CH2:21]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 57672921HCID 57672921, compound

Product 1

HCID 576729481-[[[4-(Phenylmethyl)-1-piperazinyl]carbonyl]amino]cyclohexanecarboxylic acidYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

600 ml of 1N aqueous sodium hydroxide solution was added to a solution of 7.62 g (20 mmol) of 1-[[(4-phenylmethyl-1-piperazinyl)carbonyl]amino]cyclohexanecarboxylic acid ethyl ester in 300 ml of ethanol, and the mixture was heated under reflux for 2 hours. After ether was added to the reaction solution to wash it, the aqueous layer was neutralized by concentrated hydrochloric acid and extracted with ethyl acetate. After the obtained organic layer was washed with saturated brine, it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 2.90 g (42%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. washto wash it
  4. extractionextracted with ethyl acetate
  5. washAfter the obtained organic layer was washed with saturated brine, it
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8ad22279011549038b18157ce19b3833
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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