Dichloromethane → HCID 21399508, compound

HRID 972221Notes

Reaction equation

HRID 972221 reaction equation
ClCCl.Cl([O-])(=O)(=O)=O.[CH2:9]([C:11]1(CCC#N)[C:20]2[C:19]3[NH:21][C:22]4[C:27]([C:18]=3[CH2:17][CH2:16][N+:15]=2[CH2:14][CH2:13][CH2:12]1)=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH3:10].[OH-].[Na+]>O>[CH2:9]([C:11]1([CH:13]([CH3:12])[C:14]#[N:15])[C:20]2[N:15]([CH2:16][CH2:17][C:18]3[C:19]=2[N:21]=[C:22]2[C:27]=3[CH:26]=[CH:25][CH:24]=[CH:23]2)[CH2:14][CH2:13][CH2:12]1)[CH3:10]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 21399514HCID 21399514, compound

Product 1

HCID 21399508HCID 21399508, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

40 ml. of dichloromethane are added to a suspension of 1.00 g. of 1-ethyl-1-(2-cyanoethyl)-1,2,3,4,6,7-hexahydro-12H-indolo(2,3 -a)quinolizinium perchlorate in 100 ml. of distilled water, and the pH of the mixture is adjusted to 10 to 11 with 40% sodium hydroxide solution. During this operation the mixture is cooled with water and stirred in argon atmosphere. After some minutes of stirring the separated red organic phase is removed, and the aqueous phase is extracted with 20 ml. of dichloromethane. The organic solutions are combined, dried over magnesium sulfate, and the solvent is evaporated in vacuo. The obtained 0.75 g. of red, oily residue is triturated with 1 ml. of methanol, and the resulting orange-red crystals are filtered off. 0.72 g. of (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. stirringAfter some minutes of stirring the separated red organic phase
  2. customis removed
  3. extractionthe aqueous phase is extracted with 20 ml
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent is evaporated in vacuo
  6. customof red, oily residue is triturated with 1 ml
  7. filtrationof methanol, and the resulting orange-red crystals are filtered off

Sources & evidence

ORD record
ord-8fd0853bcfe042febd549581ba0a01fa
Source dataset
uspto-grants-1977_10
Patent number
US04052404

Reaction notes

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