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

HRID 1392361Notes

Reaction equation

HRID 1392361 reaction equation
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

Participants

4

Reactant 2

HCID 166581-AminopiperidineHCID 10001752HCID 10001752, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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))

Sources & evidence

ORD record
ord-096c793d22b547f0a10f46fec0ecb020
Source dataset
uspto-grants-2008_03
Patent number
US07342032B2

Reaction notes

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