2,6-Dichloropyrazine → HCID 21906088, compound

HRID 1296646Notes

Reaction equation

HRID 1296646 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[OH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1>CCN(CC)CC>[Cl:8][C:4]1[N:3]=[C:2]([O:9][CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 785042,6-DichloropyrazineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21906088HCID 21906088, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 2,6-dichloropyrazine (5.00 g, 33.6 mmol), tert-butyl 4-hydroxy-1-piperidinecarboxylate (6.76 g, 33.6 mmol) and K-t-BuO (1 M in tert-butanol; 35 mL, 35 mmol) in Et3N (200 mL) was stirred at room temperature for 12 h. The reaction was quenched with water (50 mL) and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with saturated aqueous KH2PO4, dried (MgSO4), and concentrated in vacuo. The residue was recrystallized from ethanol/water to give 9.50 g (90%) of the title compound as a white solid: mp 86-87° C.; MS m/z 313 (M)+. Anal. (C14H20ClN3O3) C, H, N.

Workup

  1. customThe reaction was quenched with water (50 mL)
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous KH2PO4
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-4eaf1667fa414cda8e1ffcb8f0b80f4a
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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