Ammonia → 2-(3-Cyanopropyl)-4-dimethylaminomethylpyridine

HRID 1904078

Reaktionsgleichung

Reaktionsgleichung von HRID 1904078
S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[C:13]([CH2:15][CH2:16][CH2:17][C:18](O)=O)#[N:14].[CH3:21][N:22]([CH2:24][C:25]1[CH:30]=C[N:28]=[CH:27][CH:26]=1)[CH3:23].S(=O)(=O)(O)O.N>O.[N+]([O-])([O-])=O.[Ag+]>[C:13]([CH2:15][CH2:16][CH2:17][C:18]1[CH:30]=[C:25]([CH2:24][N:22]([CH3:23])[CH3:21])[CH:26]=[CH:27][N:28]=1)#[N:14]

Komponenten

8

Edukt 5

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 382394-Cyanobutanoic acidHCID 62648Ammonium PersulfateHCID 2649464-pyridinemethanamine, N,N-dimethyl-

Produkt 1

HCID 132926072-(3-Cyanopropyl)-4-dimethylaminomethylpyridineAusbeute 36,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 962WaterLösungsmittel3×

Versuchsvorschrift

Ammonium persulphate (54.8 g) in water (150 ml) and 4-cyanobutyric acid (68 g) in water (300 ml) were added separately and simultaneously over 30 minutes to a mixture of 4-dimethylaminomethylpyridine (16.32 g), silver nitrate (4 g), water (200 ml) and concentrated sulphuric acid (25 ml) stirred at 80°. The reaction mixture was stirred at 80° for 1.5 hours, cooled, poured onto crushed ice (400 g) and aqueous ammonia (28% w/w, 200 ml). The solution was extracted with chloroform (900 ml) and the chloroform extracts were washed with dilute sodium hydroxide, dried over magnesium sulphate, and concentrated in vacuo to give 2-(3-cyanopropyl)-4-dimethylaminomethylpyridine (9 g) as a clear oil b.p. 110°-112°/0.1 mm Hg.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 80° for 1.5 hours
  2. temperaturecooled
  3. additionpoured
  4. extractionThe solution was extracted with chloroform (900 ml)
  5. washthe chloroform extracts were washed with dilute sodium hydroxide
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-90ca783611704bf0ade04ddab6a76680
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04439609

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