تفاعل #74805

معادلة التفاعل

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

المذيبات

acetonitrile

acetic acid

ظروف التفاعل

المعالجة

1. 1
   أخرى26 may also be prepared
2. 2
   درجة الحرارةThe mixture is refluxed overnight
3. 3
   درجة الحرارةrefluxing
4. 4
   workup.WAITis continued for an additional day
5. 5
   درجة الحرارةThe mixture is cooled
6. 6
   أخرىevaporated
7. 7
   workup.ADDITIONWater is added to the residue
8. 8
   غسيلthe mixture is washed with diethyl ether
9. 9
   ترشيحfiltered
10. 10
    استخلاصIt is extracted with chloroform
11. 11
    أخرىthe extract dried
12. 12
    أخرىevaporated
13. 13
    workup.DISSOLUTIONthe residue is dissolved in the minimum amount of ethanol
14. 14
    أخرىthe precipitate collected
15. 15
    أخرىrecrystallized from ethanol

الإجراء التجريبي

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°.

المصدر