Methanol → 1-Ethyl-1-cyano-indolo(2,3-a)quinolizidine

HRID 223377

Reaction equation

CO.Cl([O-])(=O)(=O)=O.[CH2:8]([C:10]1([C:27]#[N:28])[C:19]2[NH+:14]([CH2:15][CH2:16][C:17]3[C:18]=2[N:20]=[C:21]2[C:26]=3[CH:25]=[CH:24][CH:23]=[CH:22]2)[CH2:13][CH2:12][CH2:11]1)[CH3:9].[B-].[Na+]>C(Cl)Cl>[CH2:8]([C:10]1([C:27]#[N:28])[CH:19]2[N:14]([CH2:15][CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][C:18]=32)[CH2:13][CH2:12][CH2:11]1)[CH3:9]

Participants

Conditions

Temperature: 5 °C

Procedure

In a 1-liter round-bottomed flask there were placed 200 ml methanol, 100 ml methylene chloride and 13.5 g (0.036 mole) of the perchlorate of step (c) above. The flask was cooled to about 5° C. and 5 g of sodium borohydrate were added in small quantities. The solution was then stirred for 2 hours at room temperature, concentrated, washed with water and extracted with methylene chloride. After drying and removing the solvent, there were obtained 8 g of yellow crystals, recrystallized from isopropyl ether, melted at 160° C. (yield 80%). The results of analysis are as follows:

Workup

customIn a 1-liter round-bottomed flask there were placed
concentrationconcentrated
washwashed with water
extractionextracted with methylene chloride
customAfter drying
customremoving the solvent

Sources & evidence

ORD record: ord-f2023747911443cb9bdc75dd5a2215be
Source dataset: uspto-grants-1982_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04353911

Linked notes

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