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

HRID 327109Notes

Reaction equation

HRID 327109 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-f3d1074084eb4814a614dca3d4e886d8
Source dataset
uspto-grants-1993_12
Patent number
US05272164

Reaction notes

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