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

HRID 1392367
Notes
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Reaction equation

HRID 1392367 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](OCC)=[O:14])=[N:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:4][CH:3]=1.[NH2:26][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13]([NH:26][N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:14])=[N:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 166581-AminopiperidineHCID 69288406Ethyl 5-(4-bromophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylate

Product 1

HCID 692884925-(4-bromophenyl)-4-(2,4-dichlorophenyl)-N-(1-piperidinyl)thiazole-2-carboxamideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Part E: A stirred mixture containing ethyl 5-(4-bromophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylate (1.00 gram, 2.2 mmol) and 1-aminopiperidine (10 mL) is heated overnight at 50° C. The resulting mixture is allowed to attain room temperature, dichloromethane is added and the resulting solution is twice washed with water, dried over MgSO4, filtered and concentrated in vacuo to give an oil. Flash chromatographic purification of this oil (ethyl acetate/petroleum ether=1/3 (v/v)) gives 5-(4-bromophenyl)-4-(2,4-dichlorophenyl)-N-(1-piperidinyl)thiazole-2-carboxamide (870 mg, 78% yield). Melting point: 171-173° C.

Workup

  1. customto attain room temperature
  2. washthe resulting solution is twice washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customFlash chromatographic purification of this oil (ethyl acetate/petroleum ether=1/3 (v/v))

Sources & evidence

ORD record
ord-0078eca3d0594822937229460eed8269
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07342032B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes