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Triethylamine → 3-Methyl 1-(4-nitrophenyl) 5-[4-(trifluoromethoxy)phenyl]piperidine-1,3-dicarboxylate

HRID 661200
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HRID 661200 반응식
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[F:14][C:15]([F:34])([F:33])[O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][NH:27][CH2:26][CH:25]([C:29]([O:31][CH3:32])=[O:30])[CH2:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl>[F:34][C:15]([F:14])([F:33])[O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][N:27]([C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[O:3])[CH2:26][CH:25]([C:29]([O:31][CH3:32])=[O:30])[CH2:24]2)=[CH:19][CH:18]=1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58002737Methyl 5-(4-(trifluoromethoxy)phenyl)piperidine-3-carboxylate

생성물 1

HCID 580025493-Methyl 1-(4-nitrophenyl) 5-[4-(trifluoromethoxy)phenyl]piperidine-1,3-dicarboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

At 0° C., 5.32 g (26.4 mmol) of 4-nitrophenyl chloroformate were added slowly to 8.0 g (26.4 mmol) of methyl 5-(4-(trifluoromethoxy)phenyl)piperidine-3-carboxylate and 5.34 g (26.3 mmol) of triethylamine in 666 ml of dichloromethane. The mixture was stirred at RT for 2 h. For workup, the reaction mixture was washed first with saturated aqueous sodium hydrogencarbonate solution, then with water. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2->1:1). Yield: 7.32 g (54% of theory)

후처리

  1. washFor workup, the reaction mixture was washed first with saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2->1:1)

출처 및 근거

ORD 기록
ord-fa4e461019b44a24b11f69a92aa2baba
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084469B2

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