Piperidine-1-carbothioamide → 4-(2-Piperidin-1-yl-thiazol-4-yl)-benzoic acid
Reaction equation
Br[CH2:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=O.[N:14]1([C:20](=[S:22])[NH2:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C1COCC1>[N:14]1([C:20]2[S:22][CH:2]=[C:3]([C:5]3[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=3)[N:21]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-(2-bromoacetyl)benzoic acid (1.23 mmol) and 1-piperidinethiocarboxamide (1.23 mmol) were mixed in THF (10 mL), then refluxed for 3 h. The reaction mixture was then allowed to reach room temperature and the obtained precipitate was collected by filtration and washed with 3 portions of diethyl ether. The crude product was crystallized from hot 1:1 EtOH-EtOAc to give a first harvest of colorless needles (0.28 g, 0.95 mmol). 1H NMR (DMSO-d6, 400 MHz,) δ 7.93 (4H, m), 7.40 (1H, s), 3.48 (4H, m), 1.60 (6H, m).