Phenyl isocyanate → HCID 70552628, compound

HRID 1702926Notes

Reaction equation

HRID 1702926 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][CH2:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][NH2:25])=[CH:11]1>CN(C)C=O>[C:1]1([NH:7][C:8]([NH:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:20][CH2:19][C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10][CH:11]=2)[CH3:26])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 2023195370684-73-0

Product 1

HCID 70552628HCID 70552628, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 ml phenyl isocyanate are added dropwise between 5° and 10° and with stirring to a solution of 5.8 g N-[2-(3-indolyl)ethyl]-N-methyl-1,3-diaminopropane in 25 ml anhydrous dimethylformamide. The solution is stirred for an hour between 10° and 15° and evaporated. The residue is dried in high vacuum and chromatographed on silicagel using methylene chloride with 6 to 10% methanol, to yield the title compound (M.pt. of the hydrogen maleate 153°-155° with decomposition after crystallization from alcohol/acetone).

Workup

  1. customevaporated
  2. customThe residue is dried in high vacuum
  3. customchromatographed on silicagel

Sources & evidence

ORD record
ord-e32b5634f28e4e5c863de5df1f1b391a
Source dataset
uspto-grants-1982_09
Patent number
US04350634

Reaction notes

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