Sodium hydride → HCID 21906088, compound

HRID 1926639Notes

Reaction equation

HRID 1926639 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[H][H].[Cl:19][C:20]1[CH:25]=[N:24][CH:23]=[C:22](Cl)[N:21]=1>CN(C=O)C>[Cl:19][C:20]1[N:21]=[C:22]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH:23]=[N:24][CH:25]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 21906088HCID 21906088, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (3.80 g, 18.9 mmol) in DMF (76 ml) was added sodium hydride (60% mineral oil dispersion; 0.906 g, 22.7 mmol) at 0° C. The reaction mixture was stirred for 1 hour, until hydrogen evolution ceased. 2,6 dichloropyrazine (2.81 g, 18.9 mmol) was added, and the reaction mixture was allowed to warm to room temperature. After 1 hour, the reaction was quenched with brine (100 mL) and extracted with EtOAc (2×200 mL). The combined EtOAc layers were dried over magnesium sulfate, filtered and concentrated to a crude residue that was purified by silica gel chromatography (EtOAc/Hexanes gradient) to afford tert-butyl 4-[(6-chloropyrazin-2-yl)oxy]piperidine-1-carboxylate as a yellow solid. LRMS calculated for C14H20ClN3O3 [M+Na]+, 336.1; found 336.1.

Workup

  1. customthe reaction was quenched with brine (100 mL)
  2. extractionextracted with EtOAc (2×200 mL)
  3. dry with materialThe combined EtOAc layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a crude residue that
  6. customwas purified by silica gel chromatography (EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-c2f358df9cfc4d0592438095f76cc133
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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