Réaction #74805

Équation de réaction

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

Solvants

acetonitrile

acetic acid

Conditions de réaction

Traitement

1. 1
   Autre26 may also be prepared
2. 2
   TempératureThe mixture is refluxed overnight
3. 3
   Températurerefluxing
4. 4
   workup.WAITis continued for an additional day
5. 5
   TempératureThe mixture is cooled
6. 6
   Autreevaporated
7. 7
   workup.ADDITIONWater is added to the residue
8. 8
   Lavagethe mixture is washed with diethyl ether
9. 9
   Filtrationfiltered
10. 10
    ExtractionIt is extracted with chloroform
11. 11
    Autrethe extract dried
12. 12
    Autreevaporated
13. 13
    workup.DISSOLUTIONthe residue is dissolved in the minimum amount of ethanol
14. 14
    Autrethe precipitate collected
15. 15
    Autrerecrystallized from ethanol

Mode opératoire

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°.

Source