2-(2-Chlorophenyl)ethylamine → HCID 10475477, compound

HRID 1720918Notes

Reaction equation

HRID 1720918 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([C:15](=[N:20][C:21]#[N:22])OCCC)[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][CH2:31][NH2:32]>CO>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([C:15](=[N:32][CH2:31][CH2:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[Cl:23])[NH:20][C:21]#[N:22])[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 831172-(2-Chlorophenyl)ethylamineHCID 10334633HCID 10334633, compound

Product 1

HCID 10475477HCID 10475477, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of propyl 5-benzylamino-N-cyano-3-pyridinecarboximidate (114 mg, 0.38 mmol) in methanol (2 ml) was added 2-(2-chlorophenyl)ethylamine (72 mg, 0.46 mmol), and the mixture was stirred for 105 minutes. 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, 20 g; eluted with chloroform:methanol=200:1) and further crystallized from diethyl ether to give the title compound (126 mg, 0.32 mmol) as colorless crystals in the yield of 85%.

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, 20 g; eluted with chloroform:methanol=200:1)
  4. customfurther crystallized from diethyl ether

Sources & evidence

ORD record
ord-218dea093501463cacc419c67d27dccd
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

Loading…