Triethylamine → 1-(6-Chloropyrazin-2-yl)piperidin-4-one

HRID 1155499Notes

Reaction equation

HRID 1155499 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C(N(CC)CC)C.O1[C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[O:19]CC1>C(#N)C>[Cl:8][C:4]1[N:3]=[C:2]([N:23]2[CH2:24][CH2:25][C:20](=[O:19])[CH2:21][CH2:22]2)[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 785042,6-Dichloropyrazine

Product 1

HCID 128022151-(6-Chloropyrazin-2-yl)piperidin-4-oneYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 3.0 g (20 mmol) 2,6-dichloropyrazine, 2.0 g (20 mmol) triethylamine, and 2.9 g (20 mmol) 1,4-dioxa-8-azaspiro[4.5]decane in 60 ml acetonitrile is refluxed 17 hours. The solvent is removed in vacuo, and the residue is dissolved in ethylacetate. After washing with water and brine, the organic fraction is dried (MgSO4) and evaporated to an oil. The oil is dissolved in 30 ml acetone and mixed with 30 ml 1N HCl. After heating this solution on the steam bath 30 minutes, the acetone is evaporated, and the concentrate is cooled to 10° C. A solid separates which is filtered and dried to afford 3 g (71%) of the desired product.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in ethylacetate
  3. washAfter washing with water and brine
  4. dry with materialthe organic fraction is dried (MgSO4)
  5. customevaporated to an oil
  6. dissolutionThe oil is dissolved in 30 ml acetone
  7. additionmixed with 30 ml 1N HCl
  8. temperatureAfter heating this solution on the steam bath 30 minutes
  9. customthe acetone is evaporated
  10. filtrationA solid separates which is filtered
  11. customdried

Sources & evidence

ORD record
ord-6d37a1a7e98e4d088599128897cb034a
Source dataset
uspto-grants-1981_11
Patent number
US04302455

Reaction notes

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