Piperidine-1-carbothioamide → 4-[2-(Piperidin-1-yl)-1,3-thiazol-4-yl]benzoic acid

HRID 606597Notes

Reaction equation

HRID 606597 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]1

Participants

4

Reactant 2

HCID 1551232Piperidine-1-carbothioamideHCID 27568364-(2-bromoacetyl)benzoic Acid

Product 1

HCID 582568994-[2-(Piperidin-1-yl)-1,3-thiazol-4-yl]benzoic acidYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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).

Workup

  1. temperaturerefluxed for 3 h
  2. customto reach room temperature
  3. filtrationthe obtained precipitate was collected by filtration
  4. washwashed with 3 portions of diethyl ether
  5. customThe crude product was crystallized from hot 1:1 EtOH-EtOAc

Sources & evidence

ORD record
ord-427eecd0f1eb4f4b8f7af32d2edb657c
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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