Acetic Acid → Benzonitrile, 4-(5,6,7,8-tetrahydroimidazo(1,5-a)pyridin-5-yl)-, hydrochloride (1:1)

HRID 477965

Reaktionsgleichung

Reaktionsgleichung von HRID 477965
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[CH:8]=[N:7][CH:6]=1.CC(C)([O-])C.[K+].C(O)(=O)C>O1CCCC1.CC(C)=O.Cl>[ClH:1].[C:17]([C:14]1[CH:15]=[CH:16][C:11]([CH:10]2[N:9]3[CH:8]=[N:7][CH:6]=[C:5]3[CH2:4][CH2:3][CH2:2]2)=[CH:12][CH:13]=1)#[N:18]

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 136882095-(3-chloropropyl) 1-(p-cyanophenylmethyl)-1H-imidazoleHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 59694Benzonitrile, 4-(5,6,7,8-tetrahydroimidazo(1,5-a)pyridin-5-yl)-, hydrochloride (1:1)

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 8.1 g of 5-(3-chloropropyl) 1-(p-cyanophenylmethyl)-1H-imidazole in 50 ml of tetrahydrofuran is cooled to 0°. To this is added 7.0 g of potassium t-butoxide as a solid in portions. The mixture is stirred at room temperature for 2 h, neutralized with 10% acetic acid and partitioned between methylene chloride and water. The organic layer is washed with water, dried over magnesium sulfate and evaporated to yield an oil which is dissolved in a small volume of acetone and neutralized with ethereal hydrogen chloride. On cooling, the title compound is obtained as a white solid, m.p. 201°-203°.

Aufarbeitung

  1. custompartitioned between methylene chloride and water
  2. washThe organic layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto yield an oil which
  6. temperatureOn cooling

Quellen und Nachweise

ORD-Eintrag
ord-01fe519c295a477cbe06cf5746c0fa05
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04889861

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