Reaction #55121

Reaction equation

hydrochloric acid

2-Chloromethylpyrazine

sodium

cysteamine hydrochloride

→

2-[(2-aminoethyl)thiomethyl]pyrazine hydrochloride

Solvents

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONhad been added gradually at 0°
2. 2
   OtherThe suspension finally obtained
3. 3
   workup.STIRRINGwas stirred at room temperature overnight
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   ExtractionThe dry residue was extracted with ethanol
6. 6
   Filtrationthe extracts filtered
7. 7
   Concentrationconcentrated
8. 8
   Otherto give the crude product
9. 9
   ExtractionExtraction with isopropyl alcohol
10. 10
    Otherwith the removal of some polymeric material
11. 11
    workup.ADDITIONthe addition of ether
12. 12
    Othergave a cream colored solid (3.5 g.), which
13. 13
    Otherwas recrystallised from ethanol-ether

Procedure

2-Chloromethylpyrazine (6.4 g.) was added over 20 minutes to a solution freshly prepared from sodium (0.23 g.) in ethanol (50 ml.) to which cysteamine hydrochloride (5.7 g.) had been added gradually at 0° and stirred at this temperature for 2 hours. The suspension finally obtained was stirred at room temperature overnight, acidified with hydrochloric acid (pH 5) and concentrated under reduced pressure. The dry residue was extracted with ethanol and the extracts filtered and concentrated to give the crude product. Extraction with isopropyl alcohol, with the removal of some polymeric material and the addition of ether gave a cream colored solid (3.5 g.), which was recrystallised from ethanol-ether to furnish 2-[(2-aminoethyl)thiomethyl]pyrazine hydrochloride, m.p. 144°-146°.

Source