Reacción #74805

Ecuación de reacción

sodium cyanoborohydride

N-methyl-ethylamine

1-(2-oxo-propyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

hydrochloric acid

sodium cyanoborohydride

→

1-[2-(N-ethyl-N-methylamino)-propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride

Disolventes

acetonitrile

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro26 may also be prepared
2. 2
   TemperaturaThe mixture is refluxed overnight
3. 3
   Temperaturarefluxing
4. 4
   workup.WAITis continued for an additional day
5. 5
   TemperaturaThe mixture is cooled
6. 6
   Otroevaporated
7. 7
   workup.ADDITIONWater is added to the residue
8. 8
   Lavadothe mixture is washed with diethyl ether
9. 9
   Filtraciónfiltered
10. 10
    ExtracciónIt is extracted with chloroform
11. 11
    Otrothe extract dried
12. 12
    Otroevaporated
13. 13
    workup.DISSOLUTIONthe residue is dissolved in the minimum amount of ethanol
14. 14
    Otrothe precipitate collected
15. 15
    Otrorecrystallized from ethanol

Procedimiento

Compound No. 26 may also be prepared as follows: 8.5 ml of glacial acetic acid are added to the solution of 8.9 g of N-methyl-ethylamine in 100 ml of acetonitrile, followed by 7.5 g of 1-(2-oxo-propyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one and 1.7 g of sodium cyanoborohydride. The mixture is refluxed overnight, an additional1.7 g of sodium cyanoborohydride is added and refluxing is continued for an additional day. The mixture is cooled, acidified to pH=1 with hydrochloric acid and evaporated. Water is added to the residue, the mixture is washed with diethyl ether, filtered and the aqueous filtrate basified to pH=10-11 with 3 N aqueous sodium hydroxide. It is extracted with chloroform, the extract dried, evaporated and the residue is dissolved in the minimum amount of ethanol. The solution is combined with 2.15 ml of 8 N ethanolic hydrochloric acid, the precipitate collected and recrystallized from ethanol, to yield the 1-[2-(N-ethyl-N-methylamino)-propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride, melting at 256°-257°.

Fuente