Phenyl isocyanate → Benzamide

HRID 344388Notes

Reaction equation

HRID 344388 reaction equation
N[C:2]1[C:24](Cl)=[CH:23][C:5]([C:6]([NH:8]CC2CCN(CCCCCCN)CC2)=[O:7])=[C:4](OC)[CH:3]=1.C1(N=C=O)C=CC=CC=1>CN(C)C=O.C(Cl)Cl>[C:6]([NH2:8])(=[O:7])[C:5]1[CH:23]=[CH:24][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 536836374-Amino-N-(1-(6-aminohexyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-Amino-N-(1-(6-aminohexyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (1.00 g) was dissolved in dimethylformamide (15 ml). A solution of phenyl isocyanate (0.30 ml) in methylene chloride was dropwise added under ice-cooling. The mixture was stirred at room temperature for 12 hr. and the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 0.30 g of 4-amino-5-chloro-2-methoxy-N-(1-(6-phenylureido)hexyl)piperidin-4-ylmethyl)benzamide.

Workup

  1. temperaturecooling
  2. concentrationand the reaction mixture was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-812adc0bbcf241febc2a03a21a4c98de
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

Loading…