Triethylamine → phenylmethyl 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylate

HRID 1698424Notes

Reaction equation

HRID 1698424 reaction equation
[NH2:1][C:2]1([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[N:25]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C(Cl)(Cl)Cl>[N:25]1([C:31]([NH:1][C:2]2([C:8]([O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 15176238Benzyl 1-aminocyclohexanecarboxylate

Product 1

HCID 17851014phenylmethyl 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylateYield 87.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

After neutralizing 203 g (500 mmol) of phenylmethyl 1-aminocyclohexanecarboxylate.p-toluenesulfonate with a 10% sodium carbonate solution, the mixture was extracted with chloroform and dried over anhydrous magnesium sulfate. The solid material was filtered off, and after adding 56 g (550 mmol) of triethylamine to the chloroform layer, 75 g (500 mmol) of 4-morpholinecarbonyl chloride was added dropwise, and the mixture was heated in an oil bath (60° C.) for 3 days. After completion of the reaction, the reaction mixture was washed successively in the order of water, a 10% aqueous potassium hydrogen sulfate solution, a saturated aqueous sodium hydrogen carbonate solution and a saturated NaCl solution, and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the resulting crystals were washed with ether to obtain 151 g (Yield: 87%) of the title compound.

Workup

  1. extractionp-toluenesulfonate with a 10% sodium carbonate solution, the mixture was extracted with chloroform
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe solid material was filtered off
  4. additionwas added dropwise
  5. customAfter completion of the reaction
  6. washthe reaction mixture was washed successively in the order of water
  7. dry with materiala 10% aqueous potassium hydrogen sulfate solution, a saturated aqueous sodium hydrogen carbonate solution and a saturated NaCl solution, and dried over anhydrous sodium sulfate
  8. customAfter removing the solvent under reduced pressure
  9. washthe resulting crystals were washed with ether

Sources & evidence

ORD record
ord-df972870077f47ca97035ffd1af56481
Source dataset
uspto-grants-2012_04
Patent number
US08163943B2

Reaction notes

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