phenylmethyl 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylate → 1-(Morpholine-4-carboxamido)cyclohexanecarboxylic acid

HRID 2053465Notes

Reaction equation

HRID 2053465 reaction equation
[N:1]1([C:7]([NH:9][C:10]2([C:16]([O:18]CC3C=CC=CC=3)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CO.[Pd]>[N:1]1([C:7]([NH:9][C:10]2([C:16]([OH:18])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 17851014phenylmethyl 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylate

Product 1

HCID 115071371-(Morpholine-4-carboxamido)cyclohexanecarboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In methanol was suspended 151 g (452 mmol) of phenylmethyl 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylate, 15 g of 5% palladium-active carbon was added to the suspension and the mixture was stirred under hydrogen stream at room temperature overnight. After removing the catalyst by filtration, the catalyst was washed three times with a mixed solvent of chloroform-methanol, and the organic layers were combined and the solvent was distilled off under reduced pressure to obtain 112 g (Yield: 100%) of the title compound.

Workup

  1. additionwas added to the suspension
  2. customAfter removing the catalyst
  3. filtrationby filtration
  4. washthe catalyst was washed three times with a mixed solvent of chloroform-methanol
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e509c080f01141928822e4ee4c7550fa
Source dataset
uspto-grants-2008_02
Patent number
US07326799B2

Reaction notes

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