Sodium Hydroxide → HCID 21406402, compound

Temperature

50 °C

2.0 g. (6.20 mmoles) of (1-ethyl-1,2,3,4,6,7-hexahydro-indolo[ 2,3-a] quinolizin-1-yl)-propionitrile are dissolved in 100 ml. of methanol, and 2 g. of Raney-nickel, thoroughly pre-washed with water and methanol, are added. The reaction mixture is warmed to 48° to 50° C under stirring, and a suspension of 2.0 g. (53 mmoles) of sodium borohydride in 8 ml. of 8 n sodium hydroxide is added. At the beginning of the reaction a vigorous bubbling can be observed. The reaction mixture is stirred for 30 minutes, thereafter it is refluxed for 3 hours. The mixture is cooled to about 50° C, and 2 g. of Raney-nickel, pre-treated as described above, and a suspension of 2.0 g. (53 mmoles) of sodium borohydride in 8 ml. of 8 n sodium hydroxide are added. When the bubbling ceases the reaction mixture is heated to boiling and refluxed for 3 hours. Thereafter the reaction mixture is cooled, the catalyst is filtered off, and washed with methanol. The filtrate is evaporated in vacuo. The oily residue is dissolved in a minimum amount of methanol, and the solution is acidified slightly by adding methanol saturated with anhydrous hydrochloric acid. The methanol solution is diluted with ether, and the precipitated hydrochloride is filtered off. The obtained salt, weighing 2.20 g., is recrystallized from a mixture of methanol and ether to obtain 1.85 g. (77.8 %) of 1-ethyl-1-(3-aminopropyl)-1,2,3,4,6,7,12,12b-octahydro-indolo(2,3-a)quinolizine dihydrochloride; m.p.: 248-251° C.

1. washof Raney-nickel, thoroughly pre-washed with water and methanol
2. additionare added
3. temperatureThe reaction mixture is warmed to 48° to 50° C
4. additiona suspension of 2.0 g
5. customAt the beginning of the reaction
6. customa vigorous bubbling can
7. stirringThe reaction mixture is stirred for 30 minutes
8. temperatureit is refluxed for 3 hours
9. additionof Raney-nickel, pre-treated
10. additiona suspension of 2.0 g
11. temperatureis heated
12. temperaturerefluxed for 3 hours
13. temperatureThereafter the reaction mixture is cooled
14. filtrationthe catalyst is filtered off
15. washwashed with methanol
16. customThe filtrate is evaporated in vacuo
17. dissolutionThe oily residue is dissolved in a minimum amount of methanol
18. additionby adding methanol saturated with anhydrous hydrochloric acid
19. additionThe methanol solution is diluted with ether
20. filtrationthe precipitated hydrochloride is filtered off
21. custom, is recrystallized from a mixture of methanol and ether
22. customto obtain 1.85 g

ORD record

ord-7ea223402ede4221972877a84447ff82

Source dataset

uspto-grants-1977_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04052404