Acetonitrile → HCID 54118437, compound

HRID 1262588Notes

Reaction equation

HRID 1262588 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 methane sulfonic 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-58cb23140b8f4ca0a765dbff34001bc7
Source dataset
uspto-grants-1984_06
Patent number
US04452808

Reaction notes

Loading…