Sodium hydride → HCID 68277999, compound

HRID 530454Notes

Reaction equation

HRID 530454 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10]C(C)(C)C)=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H-].[Na+]>O1CCOCC1>[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:24][CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 784611-Benzylpiperidin-4-olHCID 53217451tert-Butyl 6-chloropyridine-2-carboxylate

Product 1

HCID 68277999HCID 68277999, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 6-chloropyridine-2-carboxylate (1.00 g, 4.68 mmol) and N-benzylpiperidin-4-ol (1.88 g, 9.83 mmol) were dissolved in dioxane (10 mL). NaH (393 mg, 60% dispersion in mineral oil, 9.83 mmol) was added and the reaction mixture was heated using a microwave (80° C., absorption high) for 1 h. The solvents were removed in vacuo and the residue was dissolved in MeOH (100 mL), filtered and concentrated in vacuo. The residue was purified by reverse phase column chromatography to give the title compound (860 mg, 59%) as a white solid. LCMS (ES+): 313.1 [MH]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. customa microwave (80° C., absorption high) for 1 h
  3. customThe solvents were removed in vacuo
  4. dissolutionthe residue was dissolved in MeOH (100 mL)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-2b2b5ac52b6f4bf0a9936d387a79856d
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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