Dichloromethane → HCID 70633308, compound

HRID 1438875Notes

Reaction equation

HRID 1438875 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])[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 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 13026944HCID 13026944, compound

Product 1

HCID 70633308HCID 70633308, 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 a 2 n aqueous sodium hydroxide solution are added to the stirred soltion under argon atmosphere. The reaction mixture is stirred for 10 minutes, thereafter the separated organic phase is isolated and dried over anhydrous potassium carbonate. The drying agent is filtered off, 10 ml. of freshly distilled acrylonitrile are added to the filtrate, the mixture is flushed with argon, and it is allowed to stand at room temperature. The colour of the mixture turns deeper. After 2 days of standing the mixture is evaporated in vacuo at a bath temperature of maximum 40° to 50° C under argon atmosphere, and the dark red, oily residue is triturated with 5 ml. of methanol. The obtained orange red crystals, weighing 8.10 g., are filtered off, and recrystallized from 15-fold volume of methanol. 7.30 g. (79.4%) of (1-ethyl-1,2,3,4,6,7-hexahydro-12H-indolo[2,3-a]quinolizin-1-yl)-propionitrile are obtained: m.p.: 122°-123° C.

Workup

  1. customthe separated organic phase is isolated
  2. dry with materialdried over anhydrous potassium carbonate
  3. filtrationThe drying agent is filtered off
  4. additionof freshly distilled acrylonitrile are added to the filtrate
  5. customthe mixture is flushed with argon, and it
  6. customto stand at room temperature
  7. waitAfter 2 days of standing
  8. customthe mixture is evaporated in vacuo at a bath temperature of maximum 40° to 50° C under argon atmosphere
  9. customthe dark red, oily residue is triturated with 5 ml
  10. filtration, are filtered off
  11. customrecrystallized from 15-fold volume of methanol

Sources & evidence

ORD record
ord-013654b7ce10400fb4a2bd6d909094bc
Source dataset
uspto-grants-1977_11
Patent number
US04057551

Reaction notes

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