Reaktion #1445873

Reaktionsgleichung

2,4,6-cycloheptatriene-1-carbonitrile

sodium hydroxide

methylamine

→

brown oil

Ausbeute 70.0%

(1RS)-8-methyl-8-azabicyclo-[3.2.1]oct-2-ene-2-carbonitrile

Ausbeute 70.0%

Lösungsmittel

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter standing at room temperature
2. 2
   Sonstigethe methanol was evaporated
3. 3
   Extraktionfollowed by extraction with chloroform (No
4. 4
   Sonstigeof run: 2 to 5) (separation into an organic layer 1
5. 5
   Extraktionfollowed by extraction with chloroform (No
6. 6
   Sonstigeof run: 2 to 5) (separation into an organic layer 2
7. 7
   TrocknenThe organic layer 2 was dried
8. 8
   Sonstigethe solvent was evaporated

Vorschrift

In 2 ml of methanol was dissolved 0.5 g (4.27 mmol) of 2,4,6-cycloheptatriene-1-carbonitrile (4: CHT-CN). A solution of 171 mg (4.27 mmol) of sodium hydroxide in 5 ml of methanol and then 3 ml (about 38 mmol) of 40% methanolic solution of methylamine were added thereto, and the resulting mixture was stirred with heating at 125° C. for 10 hours in a sealed vessel. After standing at room temperature, the methanol was evaporated and the residue was adjusted to pH 2 with 1N sulfuric acid solution, followed by extraction with chloroform (No. of run: 1) or ether (No. of run: 2 to 5) (separation into an organic layer 1 and an aqueous layer 1). The aqueous layer 1 was neutralized with 4N sodium hydroxide solution, followed by extraction with chloroform (No. of run: 1) or ether (No. of run: 2 to 5) (separation into an organic layer 2 and an aqueous layer 2). The organic layer 2 was dried and then the solvent was evaporated therefrom to obtain 0.458 g of a brown oil (1RS)-AECG-CN (yield: 70%).

Quelle