Triethylamine → 1-[[(4-Benzoyl-1-piperazinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester

HRID 73828

반응식

HRID 73828 반응식
[C:1]1([CH2:7][O:8][C:9]([C:11]2([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:19].C(N(CC)CC)C.[C:40]([N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C(Cl)Cl>[C:1]1([CH2:7][O:8][C:9]([C:11]2([NH:17][C:18]([N:51]3[CH2:52][CH2:53][N:48]([C:40](=[O:47])[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH2:49][CH2:50]3)=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 7626541-BenzoylpiperazineHCID 15176238Benzyl 1-aminocyclohexanecarboxylate

생성물 1

HCID 576729161-[[(4-Benzoyl-1-piperazinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester수율 86.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A solution of 114 mg (0.9 mmol) of N,N-dimethylaminopyridine and 2.17 g (9.3 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester in methylene chloride was added to a solution of 2.03 g (9.3 mmol) of di-t-butyl dicarbonate in 60 ml of methylene chloride, and the mixture was stirred at room temperature for 30 minutes. Thereafter, a solution of 1.88 g (18.6 mmol) of triethylamine and 1.86 g (9.8 mmol) of 1-(benzoyl)piperazine in methylene chloride was added thereto, and the mixture was stirred at room temperature overnight. After the reaction solution was concentrated, the residue was dissolved in ethyl acetate, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained crystal was washed with diethyl ether to obtain 3.60 g (86%) of the title compound.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationAfter the reaction solution was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washthe mixture was successively washed with water
  5. dry with materialby drying with anhydrous sodium sulfate
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. washthe obtained crystal was washed with diethyl ether

출처 및 근거

ORD 기록
ord-2922b66984ce4404a06faf19cb1dcefd
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829209B2

연결된 노트

불러오는 중…