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

HRID 1392361ノート

反応式

HRID 1392361 の反応式
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

参加物

4

反応物 2

HCID 166581-AminopiperidineHCID 10001752HCID 10001752、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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))

出典と根拠

ORDレコード
ord-096c793d22b547f0a10f46fec0ecb020
出典データセット
uspto-grants-2008_03
特許番号
US07342032B2

反応ノート

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