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

HRID 606604Notes

Reaction equation

HRID 606604 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[S:16])[NH2:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Br[CH2:18][C:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)=O.C(OCC)C>C1COCC1>[NH:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:16][CH:18]=[C:19]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)[N:15]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 27568364-(2-bromoacetyl)benzoic Acid

Product 1

HCID 582568334-[2-(Piperidin-4-yl)-1,3-thiazol-4-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Thiocarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (2.47 mmol) and 4-(2-Bromo-acetyl)-benzoic acid (2.47 mmol) were mixed in THF (12 mL). After stirring at room temperature for 5 minutes the mixture was heated to 80° C. for 2 hours. The volume was reduced to 5 mL and diethylether (5 mL) was added. The mixture was then cooled to −20° C. and filtered. The solid was washed with a small amount of diethylether and dried. m/z=289.1 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification.

Workup

  1. temperaturewas heated to 80° C. for 2 hours
  2. additionwas added
  3. temperatureThe mixture was then cooled to −20° C.
  4. filtrationfiltered
  5. washThe solid was washed with a small amount of diethylether
  6. customdried
  7. customused in the next step without any further purification

Sources & evidence

ORD record
ord-caf34f261f6e4635a582fe074d6e64d6
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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