Hydrochloric Acid → 4-(3-Chloropyrazin-2-yl)cyclohexanone

HRID 2191973Notes

Reaction equation

HRID 2191973 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1.Cl>CC(C)=O>[Cl:1][C:2]1[C:7]([CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[N:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 593512402-Chloro-3-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazine

Product 1

HCID 593511294-(3-Chloropyrazin-2-yl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Chloro-3-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazine (0.29 g, 1.14 mmol) was dissolved in acetone (8 mL) and 1M aqueous hydrochloric acid (1.0 mL, 1.0 mmol) was heated to 50° C. for 4 h, then cooled to RT. The acetone was removed under vacuum and the solution was then diluted with EtOAc. This mixture was transferred to a reparatory funnel and washed with sat. aqueous sodium bicarbonate (1×), brine (1×), dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give 4-(3-chloropyrazin-2-yl)cyclohexanone.

Workup

  1. customThe acetone was removed under vacuum
  2. additionthe solution was then diluted with EtOAc
  3. customThis mixture was transferred to a reparatory funnel
  4. washwashed with sat. aqueous sodium bicarbonate (1×), brine (1×)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4811efcf22c644d690d077599074d5cd
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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