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

HRID 2263363
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2263363
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

HCID 687762351-(3-Phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylic acidAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-458fed0846324ca98cdbb615f80a59f7
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07851473B2

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