Pyridine → HCID 18688648, compound

HRID 1585804Notes

Reaction equation

HRID 1585804 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.N1C=CC=CC=1.[C:14]([C:16]1[NH:17][CH2:18][CH2:19][NH:20][CH:21]=1)#[N:15]>>[C:5]([N:17]1[CH2:18][CH2:19][NH:20][CH:21]=[C:16]1[C:14]#[N:15])(=[O:7])[CH3:6]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 117891511,4,5,6-Tetrahydro-2-pyrazinecarbonitrile

Product 1

HCID 18688648HCID 18688648, compound

Conditions

Temperature
20 °C

Procedure

10.0 ml (106 mmol) of acetic anhydride and 8.0 ml (99 mmol) of pyridine were added to 5.10 g (47 mmol) of 2-cyano-1,4,5,6-tetrahydropyrazine, and the mixture was stirred at 20° C. for 18 h. After aqueous work-up, the reaction product was extracted three times with 100-200 ml of ethyl acetate each. The combined organic extracts were dried over magnesium sulphate and concentrated. The crude product was then purified by flash chromatography (silica gel 40×3 cm, ethyl acetate:hexane=4:1, Rf =0.25). the fraction having Rf =0.25 (5.82 g) was taken up in 40 ml of diethyl ether and the precipitated solid was filtered off and dried.

Workup

  1. extractionAfter aqueous work-up, the reaction product was extracted three times with 100-200 ml of ethyl acetate each
  2. dry with materialThe combined organic extracts were dried over magnesium sulphate
  3. concentrationconcentrated
  4. customThe crude product was then purified by flash chromatography (silica gel 40×3 cm, ethyl acetate:hexane=4:1, Rf =0.25)
  5. filtrationthe precipitated solid was filtered off
  6. customdried

Sources & evidence

ORD record
ord-f166d311141c4244bffbe2fe5df66083
Source dataset
uspto-grants-1999_08
Patent number
US05939549

Reaction notes

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