1-Aminopiperidine → 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-N-(1-piperidinyl)thiazole-2-carboxamide

HRID 1392361노트

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HRID 1392361 반응식
C([O:3][C:4]([C:6]1[S:7][C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[N:10]=1)=O)C.[NH2:26][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>ClCCl>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:8]2[S:7][C:6]([C:4]([NH:26][N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:3])=[N:10][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[CH:24][CH:23]=1

참가 물질

4

반응물 2

HCID 166581-AminopiperidineHCID 10001752HCID 10001752, 화합물

생성물 1

HCID 104796865-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-N-(1-piperidinyl)thiazole-2-carboxamide수율 29%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

Part D; Ethyl-5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylate (1.00 gram, 2.42 mmol) is added to 1-aminopiperidine (10 mL) and the resulting stirred mixture is heated at 50° C. for 4 hours. Dichloromethane is added and the resulting solution is washed twice with water, dried over MgSO4, filtered and most of the dichloromethane is removed by evaporation in vacuo. Diisopropyl ether is added and the formed precipitate is removed by filtration. The filtrate is concentrated in vacuo and purified by flash chromatography (ethyl acetate: petroleum ether (40-60)=1:3 (v/v)) to produce 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-N-(1-piperidinyl)thiazole-2-carboxamide (330 mg, 29% yield) as a white foam. 1H-NMR (400 MHz, CDCl3): δ 7.92 (s, 1H), 7.47 (t, J=2 Hz, 1H), 7.24-7.32 (m, 4H), 7.13 (dt, J=8 Hz, J=2 Hz, 2H), 2.85-2.93 (m, 4H), 1.40-1.82 (m, 6H).

후처리

  1. washthe resulting solution is washed twice with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered and most of the dichloromethane
  4. customis removed by evaporation in vacuo
  5. additionDiisopropyl ether is added
  6. customthe formed precipitate is removed by filtration
  7. concentrationThe filtrate is concentrated in vacuo
  8. custompurified by flash chromatography (ethyl acetate: petroleum ether (40-60)=1:3 (v/v))

출처 및 근거

ORD 기록
ord-096c793d22b547f0a10f46fec0ecb020
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342032B2

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