2-Methoxyphenethylamine → N-cyano-N'-[2-(2-methoxyphenyl)ethyl]-4-pyridinecarboximidamide

HRID 1588553Notes

Reaction equation

HRID 1588553 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)OC(C)C)#[N:2].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][NH2:25]>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1)=[N:25][CH2:24][CH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][CH3:15])#[N:2]

Participants

4

Reactant 2

HCID 748962-MethoxyphenethylamineHCID 10012715Isopropyl N-cyano-4-pyridinecarboximidate

Product 1

HCID 19734573N-cyano-N'-[2-(2-methoxyphenyl)ethyl]-4-pyridinecarboximidamideYield 61.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl N-cyano-4-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (10 ml), and 2-(2-methoxyphenyl)ethylamine (0.44 g, 2.9 mmol) was added. The mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The residual concentrate was subjected to chromatography on a silica gel column (WAKO GEL C-200, 40 g) eluting with chloroform methanol (100:1). The eluted fractions were concentrated under reduced pressure and crystallized from chloroform-diethyl ether to give the title compound (0.45 g, 1.6 mmol, yield: 61%) as colorless crystals.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. concentrationThe residual concentrate
  3. washeluting with chloroform methanol (100:1)
  4. concentrationThe eluted fractions were concentrated under reduced pressure
  5. customcrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-7f689d2dd425486b9be76d81b13ed1d4
Source dataset
uspto-grants-1993_06
Patent number
US05223508

Reaction notes

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