Triethylamine → N-cyano-N'-(4-dimethylaminobenzyl)-3-pyridinecarboximidamide

Isopropyl N-cyano-3-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved n methanol (5 ml), and a solution of p-(dimethylamino)benzylamine dihydrochloride (0.65 g, 2.9 mmol) and triethylamine (0.64 g, 6.4 mmol) in methanol (5 ml) were added. The mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the concentrated residue thus obtained was extracted with ethyl acetate (50 ml×3). The ethyl acetate layer was washed with water (50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residual concentrate thus obtained was subjected to chromatography on a silica gel column (WAKO GEL C-200, 30 g) eluting with chloroform-methanol (100:1). The eluted fractions were concentrated under reduced pressure and then crystallized from methanol-diethyl ether to give the title compound (0.63 g, 2.3 mmol, yield: 85%) as colorless powder.

1. concentrationthe reaction solution was concentrated under reduced pressure
2. customthe concentrated residue thus obtained
3. extractionwas extracted with ethyl acetate (50 ml×3)
4. washThe ethyl acetate layer was washed with water (50 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. concentrationThe residual concentrate thus
8. customobtained
9. washeluting with chloroform-methanol (100:1)
10. concentrationThe eluted fractions were concentrated under reduced pressure
11. customcrystallized from methanol-diethyl ether

ORD-Eintrag

ord-415653bff52144268ba08504dad06867

Quelldatensatz

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05223508