Triethylamine → 4-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

HRID 876248

반응식

HRID 876248 반응식
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:44])[O:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1.C(=O)(O)[O-].[Na+]>ClCCl.O>[C:17]1([C:16]([NH:15][CH:11]2[CH2:10][CH:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:24])([F:1])[F:25])=[CH:8][CH:7]=3)[CH2:14][N:13]([C:33]([O:34][C:35]3[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=3)=[O:44])[CH2:12]2)=[O:23])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 66701397N-{5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide

생성물 1

HCID 667014674-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

At 0° C., 1.5 g (4.3 mmol) of N-{5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide and 1.2 ml (1.1 mmol) of triethylamine were initially charged in 131 ml of dichloromethane, and 868 mg (4.3 mmol) of 4-nitrophenyl chlorocarbonate were added slowly. The mixture was stirred at 0° C. for 2 h and then warmed to RT. Water and saturated aqueous sodium bicarbonate solution were added, and the reaction mixture was extracted. The organic phase was concentrated under reduced pressure and purified by column chromatography (cyclohexane/ethyl acetate 1:2). Yield: 1.95 g (88% of theory)

후처리

  1. temperaturewarmed to RT
  2. extractionthe reaction mixture was extracted
  3. concentrationThe organic phase was concentrated under reduced pressure
  4. custompurified by column chromatography (cyclohexane/ethyl acetate 1:2)

출처 및 근거

ORD 기록
ord-5ad197d86fac4986b747e1ecf455f861
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987248B2

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