Hydrochloric Acid → 1-(3-Phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylic acid

HRID 2263363Notes

Reaction equation

HRID 2263363 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:13][CH2:14][CH:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17]3)[S:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68779858Ethyl 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylate

Product 1

HCID 687762351-(3-Phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylate (1.12 g, 3.53 mmol), an aqueous 2 N sodium hydroxide solution (4 ml), tetrahydrofuran (20 ml) and ethanol (12 ml) was stirred at 80° C. for 1 hour. Thereto 2 N hydrochloric acid (4 ml) was added and the solvent was distilled off under reduced pressure. The residue was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and ethyl acetate to yield 910 mg (89.2%) of the desired product.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionThe residue was poured to water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-458fed0846324ca98cdbb615f80a59f7
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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