Propyl isocyanate → 4-amino-5-chloro-2-methoxy-N-(1-(4-(3-n-propylureido)butyl)-piperidin-4-ylmethyl)benzamide

HRID 344329Notes

Reaction equation

HRID 344329 reaction equation
[NH2:1][C:2]1[C:22]([Cl:23])=[CH:21][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:24][CH3:25])[CH:3]=1.[CH2:26]([N:29]=[C:30]=[O:31])[CH2:27][CH3:28]>CN(C)C=O>[NH2:1][C:2]1[C:22]([Cl:23])=[CH:21][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:30]([NH:29][CH2:26][CH2:27][CH3:28])=[O:31])[CH2:14][CH2:15]2)=[O:7])=[C:4]([O:24][CH3:25])[CH:3]=1

Participants

4

Reactant 2

HCID 61033Propyl isocyanateHCID 541388784-amino-N-(1-(4-aminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 540797934-amino-5-chloro-2-methoxy-N-(1-(4-(3-n-propylureido)butyl)-piperidin-4-ylmethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-N-(1-(4-aminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (1.0 g) was dissolved in dimethylformamide (10 ml) and n-propyl isocyanate (0.26 ml) was dropwise added under ice-cooling. The mixture was stirred at room temperature for 1 hr, and the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 0.2 g of 4 -amino-5-chloro-2-methoxy-N-(1-(4-(3-n-propylureido)butyl)-piperidin-4-ylmethyl)benzamide.

Workup

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

Sources & evidence

ORD record
ord-6117365330154ef992adf94be8bfd22a
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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