1-Phenylpiperazine → 1-[[(4-Phenyl-1-piperazinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester

HRID 448732노트

반응식

HRID 448732 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]1([N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[C:1]1([CH2:7][O:8][C:9]([C:11]2([NH:17][C:18]([N:49]3[CH2:50][CH2:51][N:46]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH2:47][CH2:48]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 70961-PhenylpiperazineHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 15176238Benzyl 1-aminocyclohexanecarboxylate

생성물 1

HCID 576728411-[[(4-Phenyl-1-piperazinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester수율 70.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A solution of 366 mg (3 mmol) of N,N-dimethylaminopyridine and 6.99 g (30 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester in methylene chloride was added to a solution of 6.55 g (30 mmol) of di-t-butyl dicarbonate in 150 ml of methylene chloride, and the mixture was stirred at room temperature for 30 minutes. Thereafter, a solution of 6.07 g (60 mmol) of triethylamine and 5.11 g (33 mmol) of 1-phenylpiperazine in methylene chloride was added, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated, ethyl acetate was added thereto, and the mixture was successively washed with water, 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 8.88 g (70%) of the title compound.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe reaction solution was concentrated
  3. additionethyl acetate was added
  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-a18c4306a07f40c9b5921a72f2bcc5ba
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481725B2

반응 노트

불러오는 중…