Dichloromethane → HCID 21399508, compound

HRID 972219Notes

Reaction equation

HRID 972219 reaction equation
Cl([O-])(=O)(=O)=O.[CH2:6]([CH:8]1[C:17]2[C:16]3[NH:18][C:19]4[C:24]([C:15]=3[CH2:14][CH2:13][N+:12]=2[CH2:11][CH2:10][CH2:9]1)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH3:7].ClCCl.[OH-].[Na+]>O>[CH2:6]([C:8]1([CH:10]([CH3:9])[C:11]#[N:12])[C:17]2[N: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]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 13026944HCID 13026944, compound

Product 1

HCID 21399508HCID 21399508, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.0 g. (28.5 mmoles) of 1-ethyl-2,3,4,6,7,12-hexahydro-indolo(2,3 -a)quinolizinium perchlorate are dissolved in 100 ml. of dichloromethane, and 75 ml. of distilled water and 20 ml. of 2 n sodium hydroxide are added to the solution 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, 10 ml. (142 mmoles) of freshly distilled acrylonitrile are added to the filtrate, the mixture is flushed with argon, and allowed to stand at room temperature for 2 days, during which period the solution darkens considerably. Thereafter the solution is evaporated in vacuo under argon atmosphere (bath temperature: maximum 40° to 50° C). The residual dark red oil is triturated with 5 ml. of methanol, and the formed orange-red crystals are filtered off. The thus-obtained crude product, weighing 8.10 g., is recrystallized from 15-fold volume of methanol. 7.30 g. (79.4 %) of crystalline (1-ethyl-1,2,3,4,6,7-hexahydro-indolo[2,3-a]quinolizin-1-yl)-propionitrile are obtained; m.p.: 122-123° 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(142 mmoles) of freshly distilled acrylonitrile are added to the filtrate
  6. customthe mixture is flushed with argon
  7. customThereafter the solution is evaporated in vacuo under argon atmosphere (bath temperature: maximum 40° to 50° C)
  8. customThe residual dark red oil is triturated with 5 ml
  9. filtrationof methanol, and the formed orange-red crystals are filtered off
  10. customThe thus-obtained crude product
  11. custom, is recrystallized from 15-fold volume of methanol

Sources & evidence

ORD record
ord-437b7eba08aa4f97afde9e767986802c
Source dataset
uspto-grants-1977_10
Patent number
US04052404

Reaction notes

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