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

HRID 1698424ノート

反応式

HRID 1698424 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-df972870077f47ca97035ffd1af56481
出典データセット
uspto-grants-2012_04
特許番号
US08163943B2

反応ノート

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