Reaktion #734648

Reaktionsgleichung

1-ethyl-hexahydro-azepin-4-one

tert.butylnitrite

amino-acetonitrile hydrochloride

N-ethyl-diisopropylamine

→

desired compound

7-Ethyl-2-amino-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine-1-oxide dihydrochloride

Lösungsmittel

tetrahydrofuran

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture was refluxed for 4 hours
2. 2
   Filtrationfiltered
3. 3
   Sonstigethe filtrate was evaporated

Vorschrift

First 23 gm (0.16 mol) of 1-ethyl-hexahydro-azepin-4-one and then 19.2 ml of tert.butylnitrite were added dropwise to a mixture of 19 gm (0.16 mol) of potassium tert.butylate and 200 ml of absolute tetrahydrofuran at -40° C., and the resulting mixture was allowed to stand overnight at 0° to 10° C. Thereafter, a solution of 20 gm (0.217 mol) of amino-acetonitrile hydrochloride and 30 gm of N-ethyl-diisopropylamine in 280 ml of chloroform was added, and the resulting mixture was refluxed for 4 hours, then filtered, and the filtrate was evaporated. The desired compound was isolated from the isomer mixture residue by silicagel chromatography with acetone/concentrated ammonia (95:5). The dihydrochloride was precipitated from ethanol with ethanolic hydrochloric acid.

Quelle