Potassium Carbonate → HCID 21436047, compound

HRID 2397576Notes

Reaction equation

HRID 2397576 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=3)[N:9]([CH2:17][CH2:18][NH2:19])[C:8]=2[C:20](OCC)=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:10][N:9]([CH3:17])[CH2:8][CH2:7][CH2:1][N:19]1[CH2:18][CH2:17][N:9]2[C:10]3[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][C:15]=3[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:8]2[C:20]1=[O:21]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 15733261HCID 15733261, compound

Product 1

HCID 21436047HCID 21436047, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 3-phenyl-5-chloro-1-(2-aminoethyl)indole-2-carboxylate (6 grams, 0.019 mole) in 50 ml dimethyl formamide is added potassium carbonate, powdered, 3.4 grams (0.025 mole), followed by 2.45 grams (0.02 mole) distilled dimethylaminopropyl chloride. The solution is stirred 56 hours at room temperature, then heated at 100°-120° C. for 4 hours. After cooling, the suspension is poured into 200 ml ice-water and extracted with dichloromethane. The extract is washed with saline, then dried over sodium sulfate, filtered and concentrated. The residue, which contains considerable dimethyl formamide, is poured into water (300 ml). A solid is formed and is separated by decantation. The residue is crystallized from acetone.

Workup

  1. distillationdistilled dimethylaminopropyl chloride
  2. temperatureheated at 100°-120° C. for 4 hours
  3. temperatureAfter cooling
  4. additionthe suspension is poured into 200 ml ice-water
  5. extractionextracted with dichloromethane
  6. washThe extract is washed with saline
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionis poured into water (300 ml)
  11. customA solid is formed
  12. customis separated by decantation
  13. customThe residue is crystallized from acetone

Sources & evidence

ORD record
ord-d527dd94512044ffb995e855d5d72cbb
Source dataset
uspto-grants-1977_05
Patent number
US04022778

Reaction notes

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