Acetonitrile → HCID 54118437, compound

HRID 280273Notes

Reaction equation

HRID 280273 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.[CH2:14](Br)[CH:15]=[CH2:16].C(N([CH2:23][CH3:24])CC)C.[C:25](#N)C>>[CH2:14]([N:1]([CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2)[CH2:25][CH:23]=[CH2:24])[CH:15]=[CH2:16]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 7841Allyl bromideHCID 8471TriethylamineHCID 233220374-Aminoethyl-2(3H)-indolone

Product 1

HCID 54118437HCID 54118437, compound

Procedure

4-Aminoethyl-2(3H)-indolone (10 g) is reacted with two mole equivalents of allyl bromide and 4 equivalents of triethylamine in acetonitrile with mild heat for several hours. The reaction mixture is evaporated. The residue is suspended in water. The mixture is extracted with ethyl acetate. The extracts are washed, dried and evaporated to give 4-di-allylaminoethyl-2(3H)-indolone. This material (1 g) is dissolved in ether-ethanol and treated with methanesulfonic acid to give the methane sulfonate salt. Using benzyl bromide gives 4-dibenzylaminoethyl-2(3H)-indolone.

Workup

  1. temperaturewith mild heat for several hours
  2. customThe reaction mixture is evaporated
  3. extractionThe mixture is extracted with ethyl acetate
  4. washThe extracts are washed
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-c1d5b64ed2c04dca98fe4553de56e2c6
Source dataset
uspto-grants-1986_05
Patent number
US04588740

Reaction notes

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