Phenethylamine → N-Cyano-N'-(2-phenylethyl)pyridine-3-carboximidamide

HRID 374158Notes

Reaction equation

HRID 374158 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)OC(C)C)#[N:2].[C:15]1([CH2:21][CH2:22][NH2:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[N:23][CH2:22][CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[N:2]

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester

Product 1

HCID 131608N-Cyano-N'-(2-phenylethyl)pyridine-3-carboximidamideYield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl N-cyano-3-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (10 ml), and 2-phenylethylamine (0.35 g, 2.9 mmol) was added. The mixture was stirred at room temperature for 40 minutes. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the concentrated residue thus obtained was crystallized from methanol-diethyl ether to give the title compound (0.45 g, 1.8 mmol, yield: 68%) as colorless needles.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe concentrated residue thus obtained
  3. customwas crystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-6154a2109de24baaaca97563e93ddc14
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Reaction notes

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