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

HRID 1392367Notes

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

Participants

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

customto attain room temperature
washthe resulting solution is twice washed with water
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give an oil
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

Loading…