2-(2-Chlorophenyl)ethylamine → HCID 10359994, compound

HRID 1720916Notes

Reaction equation

HRID 1720916 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([NH:15][CH:16]([CH3:18])[CH3:17])[CH:14]=1)OCCC)#[N:2].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH2:27][NH2:28]>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([NH:15][CH:16]([CH3:17])[CH3:18])[CH:14]=1)=[N:28][CH2:27][CH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[Cl:19])#[N:2]

Participants

4

Reactant 2

HCID 831172-(2-Chlorophenyl)ethylamineHCID 10332165HCID 10332165, compound

Product 1

HCID 10359994HCID 10359994, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of propyl N-cyano-5-isopropylamino-3-pyridinecarboximidate (98 mg, 0.42 mmol) in methanol (3 ml) was added 2-(2-chlorophenyl)ethylamine (79 mg, 0.51 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, 30 g; eluted with chloroform:methanol=100:1) and further crystallized from diethyl ether to give the title compound (110 mg, 0.34 mmol) as colorless crystals in the yield of 80%.

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=100:1)
  4. customfurther crystallized from diethyl ether

Sources & evidence

ORD record
ord-c34a764ab9894e9b80a319ee7598d25d
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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