2-(2-Chlorophenyl)ethylamine → 5-n-butylamino-N-cyano-N'-[2-(2-chlorophenyl)ethyl]-3-pyridinecarboximidamide

HRID 1720917Notes

Reaction equation

HRID 1720917 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([C:12](=[N:17][C:18]#[N:19])OCCC)[CH:9]=[N:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH2:28][NH2:29]>CO>[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([C:12](=[N:29][CH2:28][CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[Cl:20])[NH:17][C:18]#[N:19])[CH:9]=[N:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 831172-(2-Chlorophenyl)ethylamineHCID 10083970propyl 5-n-butylamino-N-cyano-3-pyridinecarboximidate

Product 1

HCID 104508845-n-butylamino-N-cyano-N'-[2-(2-chlorophenyl)ethyl]-3-pyridinecarboximidamideYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of propyl 5-n-butylamino-N-cyano-3-pyridinecarboximidate (99 mg, 0.38 mmol) in methanol (2 ml) was added 2-(2-chlorophenyl)ethylamine (71 mg, 0.46 mmol), and the mixture was stirred for 2 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure and the residue obtained was purified by silica gel column chromatography (Wako Gel C-200, 30 g; eluted with chloroform:methanol=200:1) and further crystallized from diethyl ether to give the title compound (90 mg, 0.25 mmol) as colorless crystals in the yield of 67%.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. customwas purified by silica gel column chromatography (Wako Gel C-200, 30 g; eluted with chloroform:methanol=200:1)
  4. customfurther crystallized from diethyl ether

Sources & evidence

ORD record
ord-ad8a9f55731c4169a9bcffc38d1403ed
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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