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

HRID 223378Notes

Reaction equation

HRID 223378 reaction equation
Cl([O-])(=O)(=O)=O.[CH2:6]([C:8]1([C:25]#[N:26])[C:17]2[NH+:12]([CH2:13][CH2:14][C:15]3[C:16]=2[N:18]=[C:19]2[C:24]=3[CH:23]=[CH:22][CH:21]=[CH:20]2)[CH2:11][CH2:10][CH2:9]1)[CH3:7].Cl>[Zn].C(O)C>[CH2:6]([C:8]1([C:25]#[N:26])[CH:17]2[N:12]([CH2:13][CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][C:16]=32)[CH2:11][CH2:10][CH2:9]1)[CH3:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1317128541-Ethyl-1-cyano-5.12b-didehydro-indolo(2,3-a)quinolizidinium perchlorate

Product 1

HCID 128664501-Ethyl-1-cyano-indolo(2,3-a)quinolizidineYield 71.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

In a 1-liter flask there was placed 19 g of the perchlorate of step (c) above, 300 cc of 95% ethanol and 40 g of zinc powder. There was added from a flask 100 ml of concentrated hydrochloric acid. Mild reflux could be observed during the addition of the acid. The mixture was allowed to stand at room temperature for 10 hours. It was then concentrated, washed with water and extracted with methylene chloride. It was made alkaline with sodium hydroxide and filtered through Celite (Trade Mark). After decanting, drying and evaporating the solvents there were obtained 6 g of a product, insoluble in ether, melting at 250° C. The results of analysis are as follows:

Workup

  1. customIn a 1-liter flask there was placed
  2. temperatureMild reflux could
  3. additionbe observed during the addition of the acid
  4. concentrationIt was then concentrated
  5. washwashed with water
  6. extractionextracted with methylene chloride
  7. filtrationfiltered through Celite (Trade Mark)
  8. customAfter decanting
  9. customdrying
  10. customevaporating the solvents

Sources & evidence

ORD record
ord-b9d3cfe9fa584d6a90d188025c52ca92
Source dataset
uspto-grants-1982_10
Patent number
US04353911

Reaction notes

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