Reacción #1375299

Ecuación de reacción

sodium hydroxide

1,2,4,5-tetrahydro-11-methyl-3H-azepino[4,5-b]quinoline

ethyl chloroformate

→

1,2,4,5-Tetrahydro-11-methyl-3-azepino[4,5-b]quinoline-carboxylic acid ethyl ester hydrochloride

Disolventes

benzene

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter refluxing the resulting mixture for 2 hours
2. 2
   OtroThe benzene layer was separated
3. 3
   Extracciónthe aqueous layer was extracted with chloroform
4. 4
   SecadoThe combined benzene and chloroform phases were dried over sodium sulfate
5. 5
   workup.DISTILLATIONthe solvents were distilled off
6. 6
   Otrocrystallized out
7. 7
   workup.DISSOLUTIONFor conversion into the hydrochloride, 11 gm of the base were dissolved in 60 ml of isopropanol
8. 8
   Filtraciónthe solution was filtered
9. 9
   workup.ADDITION10 ml of isopropanolic hydrochloric acid were added
10. 10
    OtroThe hydrochloride crystallized out of the hot solution

Procedimiento

11 gm (51.7 millimols) of 1,2,4,5-tetrahydro-11-methyl-3H-azepino[4,5-b]quinoline were dissolved in 275 ml of hot benzene, and then a solution of 9.8 ml (103.4 millimols) of ethyl chloroformate in 70 ml of benzene were simultaneously added dropwise. After refluxing the resulting mixture for 2 hours, 150 ml of ice water were added to the cooled reaction mixture, and the aqueous mixture was made alkaline with 2 N sodium hydroxide. The benzene layer was separated and the aqueous layer was extracted with chloroform. The combined benzene and chloroform phases were dried over sodium sulfate, the solvents were distilled off, and the residual oil was admixed with ether, whereupon 11 gm (75% of theory) of the base, m. p. 126° C., crystallized out. For conversion into the hydrochloride, 11 gm of the base were dissolved in 60 ml of isopropanol, the solution was filtered, and 10 ml of isopropanolic hydrochloric acid were added. The hydrochloride crystallized out of the hot solution. Yield: 12 gm (72% of theory); m.p. 247° C. (decomp.).

Fuente