Potassium Iodide → N-benzyl-N-(5,6-dimethoxy-1-indanyl)glycine hydrochloride

HRID 1248048Notes

Reaction equation

HRID 1248048 reaction equation
[ClH:1].[CH2:2]([NH:9][CH:10]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:32][C:33]([O:35]CC)=[O:34]>C(O)C>[ClH:1].[CH2:2]([N:9]([CH:10]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][CH2:11]1)[CH2:32][C:33]([OH:35])=[O:34])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 202808021-Benzylamino-5,6-dimethoxyindane hydrochloride

Product 1

HCID 20280785N-benzyl-N-(5,6-dimethoxy-1-indanyl)glycine hydrochlorideYield 69.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 17 g of 1-benzylamino-5,6-dimethoxyindane hydrochloride in 300 ml of ethanol are added 10 g of potassium carbonate, 3.0 g of potassium iodide and 17 g of ethyl bromoacetate, and the mixture is refluxed for 8 hours. The ethanol is distilled off under reduced pressure, 500 ml of ice-water is added to the residue, and extraction with 500 ml of ethyl acetate is carried out. After the extract is washed with water and dried, the ethyl acetate is distilled off under reduced pressure. The residue is dissolved in 200 ml of ethanol. To the solution are added 5.0 g of sodium hydroxide and 10 ml of water, and the mixture is refluxed for 2 hours. Thereafter, the ethanol is evaporated under reduced pressure, and the residue is dissolved in 300 ml of water. The mixture is neutralized with acetic acid, and subjected to extraction with 300 ml of chloroform. After the extract is washed with water and dried, the chloroform is distilled off. To the residue are added 20 ml of 20% alcoholic hydrochloric acid and 200 ml of ethyl ether, and the mixture is allowed to stand. Collection of the crystalline precipitates by filtration gives 14 g of N-benzyl-N-(5,6-dimethoxy-1-indanyl)glycine hydrochloride as colorless needles. Melting point: 174°-177° C.

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. distillationThe ethanol is distilled off under reduced pressure, 500 ml of ice-water
  3. additionis added to the residue, and extraction with 500 ml of ethyl acetate
  4. washAfter the extract is washed with water
  5. customdried
  6. distillationthe ethyl acetate is distilled off under reduced pressure
  7. dissolutionThe residue is dissolved in 200 ml of ethanol
  8. additionTo the solution are added 5.0 g of sodium hydroxide and 10 ml of water
  9. temperaturethe mixture is refluxed for 2 hours
  10. customThereafter, the ethanol is evaporated under reduced pressure
  11. dissolutionthe residue is dissolved in 300 ml of water
  12. extractionsubjected to extraction with 300 ml of chloroform
  13. washAfter the extract is washed with water
  14. customdried
  15. distillationthe chloroform is distilled off
  16. additionTo the residue are added 20 ml of 20% alcoholic hydrochloric acid and 200 ml of ethyl ether
  17. customCollection of the
  18. customcrystalline precipitates by filtration

Sources & evidence

ORD record
ord-28eb0b79f6cc4a2fb3473a90b64563c8
Source dataset
uspto-grants-1985_06
Patent number
US04521607

Reaction notes

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