Acetyl chloride → 1-(4-(3-Fluoropyrazin-2-yl)piperidin-1-yl)ethanone

HRID 2192009Notes

Reaction equation

HRID 2192009 reaction equation
[F:1][C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22]>C(Cl)Cl>[F:1][C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][N:11]([C:21](=[O:23])[CH3:22])[CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 669860512-Fluoro-3-(4-piperidinyl)pyrazine

Product 1

HCID 593512871-(4-(3-Fluoropyrazin-2-yl)piperidin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-fluoro-3-(piperidin-4-yl)pyrazine (0.311 g, 1.716 mmol) dissolved in DCM (5 mL) was added triethylamine (0.286 mL, 2.06 mmol), then acetyl chloride, reagent grade (0.134 mL, 1.89 mmol). The reaction mixture was stirred at RT for 1 h then partitioned between DCM and water. The aqueous layer was extracted with DCM (3×) and the combined organic layer was washed with brine, dried (Na2SO4) and concentrated to give 1-(4-(3-fluoropyrazin-2-yl)piperidin-1-yl)ethanone as a yellow oil. MS (ESI, pos. ion) m/z: 224.0 (M-56).

Workup

  1. customthen partitioned between DCM and water
  2. extractionThe aqueous layer was extracted with DCM (3×)
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f0a1a68849d34624b617ab5398fa5c6f
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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