Hydrochloric Acid → 4-(4-Ethenyl-2-thiazolyl)piperidine

HRID 238657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238657
[CH:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[S:6][CH:7]=1)=[CH2:2].Cl.C(OCC)C.[OH-].[Na+]>ClCCl>[CH:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[S:6][CH:7]=1)=[CH2:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 687436451,1-Dimethylethyl 4-(4-ethenyl-2-thiazolyl)-1-piperidinecarboxylate2×

Produkt 1

HCID 687444094-(4-Ethenyl-2-thiazolyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1,1-dimethylethyl 4-(4-ethenyl-2-thiazolyl)-1-piperidinecarboxylate (i.e. the product of Example 4, Step A) (471 mg, 1.6 mmol) in dichloromethane (5 mL) was added a solution of hydrogen chloride in diethyl ether (2.0 M, 7 mL, 14 mmol). The reaction mixture was stirred under nitrogen at room temperature for 4 h, and then 1 N aqueous sodium hydroxide solution was added until pH of the reaction mixture increased to about 10. The resulting mixture was extracted with dichloromethane (2×). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give 302 mg of the title compound as an oil.

Aufarbeitung

  1. temperatureincreased to about 10
  2. extractionThe resulting mixture was extracted with dichloromethane (2×)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a14e330f38d94452b6470ef94c6bee48
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642634B2

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