Ammonia → HCID 23457303, compound

HRID 1680177Notes

Reaction equation

HRID 1680177 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[CH2:17][C:18]#[N:19].N.[H][H]>C(O)CC.[Ni]>[NH2:19][CH2:18][CH2:17][CH:3]1[CH:2]([CH3:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 23457308HCID 23457308, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23457303HCID 23457303, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 10311-PropanolSolvent

Procedure

To a solution of 83 g of 3-methyl-1-phenyl-2-indole acetonitrile in 340 ml of n-propanol there are added 100 ml of concentrated aqueous ammonia and two spoons of Raney nickel. The mixture is hydrogenated at 60° and normal pressure. After the hydrogen take-up is complete, filtration is effected and the filtrate is made slightly acid with glacial acetic acid under cooling. After the addition of water, washing with diethyl ether is effected and the aqueous phase is made alkaline with dilute ammonia. The latter is extracted with methylene chloride and the extract is concentrated by evaporation after washing with water and drying over sodium sulphate. The residue, 2-aminoethyl-3-methyl-1-phenylindole, is then converted into the hydrochloride. M.Pt. 202°-207° (from acetone/diethyl/ether).

Workup

  1. customis hydrogenated at 60°
  2. filtrationfiltration
  3. temperatureunder cooling
  4. additionAfter the addition of water
  5. washwashing with diethyl ether
  6. extractionThe latter is extracted with methylene chloride
  7. concentrationthe extract is concentrated by evaporation
  8. washafter washing with water
  9. dry with materialdrying over sodium sulphate

Sources & evidence

ORD record
ord-d785ec12f02e420bb204f1e4ca751f45
Source dataset
uspto-grants-1981_06
Patent number
US04272533

Reaction notes

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