Dichloromethane → HCID 21399512, compound

HRID 972220Notes

Reaction equation

HRID 972220 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH2:6]([CH:10]1[C:19]2[C:18]3[NH:20][C:21]4[C:26]([C:17]=3[CH2:16][CH2:15][N+:14]=2[CH2:13][CH2:12][CH2:11]1)=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:7][CH2:8][CH3:9].ClCCl.[OH-].[Na+]>O>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH2:6]([C:10]1([CH2:11][CH2:12][C:13]#[N:14])[C:19]2[C:18]3[NH:20][C:21]4[C:26]([C:17]=3[CH2:16][CH2:15][N+:14]=2[CH2:13][CH2:12][CH2:11]1)=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 21399502HCID 21399502, compound

Product 1

HCID 21399512HCID 21399512, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g. (13.3 mmoles) of 1-n-butyl-2,3,4,6,7,12-hexahydro-indolo(2,3 -a)quinolizinium perchlorate are suspended in 50 ml. of dichloromethane, and 50 ml. of distilled water and 10 ml. of 2 n sodium hydroxide are added to the suspension under constant stirring in argon atmosphere. The reaction mixture is stirred for 10 minutes, thereafter the organic phase is separated, and dried over anhydrous potassium carbonate. The drying agent is filtered off, 5.0 ml. (71 mmoles) of freshly distilled acrylonitrile are added to the filtrate, the mixture is flushed with argon, and allowed to stand at room temperature for 3 days. Thereafter the reaction mixture is evaporated in vacuo, the red oily residue is dissolved in 5 ml. of methanol, and the solution is acidified to pH = 6 with 70% perchloric acid. The crystallization of the product is initiated by scraping the wall of the flask. The flask is put into refrigerator. The separated yellow crystals are filtered off, washed with cold methanol, and the obtained 4.20 g. of product (m.p.: 215-220° C) are recrystallized from 5-fold volume of methanol. 3.70 g. (64.1 %) of 1-n-butyl-1-(2-cyanoethyl)- 1,2,3,4,6,7-hexahydro- 12H-indolo(2,3 -a)quinolizinium perchlorate are obtained in the form of yellow needles; m.p.: 224-226° C.

Workup

  1. stirringThe reaction mixture is stirred for 10 minutes
  2. customthe organic phase is separated
  3. dry with materialdried over anhydrous potassium carbonate
  4. filtrationThe drying agent is filtered off
  5. addition(71 mmoles) of freshly distilled acrylonitrile are added to the filtrate
  6. customthe mixture is flushed with argon
  7. customThereafter the reaction mixture is evaporated in vacuo
  8. dissolutionthe red oily residue is dissolved in 5 ml
  9. customThe crystallization of the product
  10. filtrationThe separated yellow crystals are filtered off
  11. washwashed with cold methanol
  12. customof product (m.p.: 215-220° C) are recrystallized from 5-fold volume of methanol

Sources & evidence

ORD record
ord-358519dd92c6489289ac624a2418a9ea
Source dataset
uspto-grants-1977_10
Patent number
US04052404

Reaction notes

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