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

HRID 1698425Notes

Reaction equation

HRID 1698425 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 phenyl-methyl 1-[N-(morpholine-4-carbonyl)amino]cyclohexane-carboxylate, 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-4324349418f64462ae875e7860bbd20e
Source dataset
uspto-grants-2012_04
Patent number
US08163943B2

Reaction notes

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