Hydrochloric Acid → HCID 58945860, Verbindung

HRID 2267147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2267147
[C:1]([C:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH:8]=1)#[N:2].[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-].[NH4+].[OH-].[Na+].Cl.C(O[CH2:29][CH3:30])(=O)C>CN(C)C=O>[C:30]1([N:18]2[N:17]=[N:16][C:1]([C:3]3[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH:4]=3)=[N:2]2)[CH:29]=[CH:7][CH:8]=[CH:3][CH:1]=1

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68431027tert-Butyl 4-cyano-3,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 58945860HCID 58945860, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

Dimethylformamide (2 m) was added to 104 mg of tert-butyl 4-cyano-1,2,3,6-tetrahydropyridine-1-carboxylate prepared in 1) of Example 23, 310 mg of sodium azide and 260 mg of ammonium chloride and the mixture was stirred at 115° C. for 3 hours. After cooling down to room temperature, ethyl acetate and a 2N aqueous solution of sodium hydroxide were added thereto. After the aqueous layer was neutralized with a 1N aqueous solution of hydrochloric acid, the product was extracted with chloroform. The extract was dried over sodium sulfate, the solvent was evaporated in vacuo and the resulting residue was purified by a silica gel thin-layer chromatography (chloroform/methanol=7/1) to give 12 mg of the title compound as a crude product.

Aufarbeitung

  1. temperatureAfter cooling down to room temperature
  2. extractionthe product was extracted with chloroform
  3. dry with materialThe extract was dried over sodium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customthe resulting residue was purified by a silica gel thin-layer chromatography (chloroform/methanol=7/1)

Quellen und Nachweise

ORD-Eintrag
ord-e04bded078fb455ea8734d0ca2ccc367
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858800B2

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