Ammonia → 1-(2-Aminoethyl)-6-methoxyindan

HRID 1762577Notes

Reaction equation

HRID 1762577 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][C:13]#[N:14])=[CH:5][CH:4]=1.N>CO.[Ni]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][CH2:13][NH2:14])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 130459302-(6-Methoxyindan-1-yl)acetonitrile

Product 1

HCID 110196681-(2-Aminoethyl)-6-methoxyindan

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

9.3 g (49 mmol) of crude 2-(6-methoxyindan-1-yl)acetonitrile are dissolved in 100 ml of methanol and, after the addition of 1 g of Raney nickel and 20 g of liquid ammonia, are hydrogenated at 70°-80° and 120 bar pressure. After 3 hours, the catalyst is filtered off from the methanolic solution and is subsequently washed with methanol. The methanolic solutions are combined and rendered acidic with hydrochloric acid. The acidic solution is concentrated to dryness by evaporation in vacuo, and the residue is dissolved in 100 ml of water, rendered alkaline with concentrated sodium hydroxide solution and extracted by shaking with diethyl ether. The ethereal phases are washed with saturated sodium chloride solution and dried over magnesium sulphate. After removing the solvent, crude 2-(6-methoxyindan-1-yl)ethylamine is obtained in the form of a yellow oil.

Workup

  1. customare hydrogenated at 70°-80°
  2. filtrationthe catalyst is filtered off from the methanolic solution
  3. washis subsequently washed with methanol
  4. concentrationThe acidic solution is concentrated to dryness by evaporation in vacuo
  5. dissolutionthe residue is dissolved in 100 ml of water
  6. extractionextracted
  7. washThe ethereal phases are washed with saturated sodium chloride solution
  8. dry with materialdried over magnesium sulphate
  9. customAfter removing the solvent

Sources & evidence

ORD record
ord-a46de89294de430087a61826908ec2c4
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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