Sodium hydride → 1-Boc-4-(2-pyridyloxy)piperidine

HRID 1815061Notes

Reaction equation

HRID 1815061 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl.Cl[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 156199202-Chloropyridine--hydrogen chloride (1/1)

Product 1

HCID 219060391-Boc-4-(2-pyridyloxy)piperidineYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-t-Butoxycarbonyl-4-piperidinol (5.0 g, 24.88 mmol) in dry dimethylformamide (60 mL) was treated with sodium hydride (60%, 2.99 g, 74.75 mmol) at room temperature under argon and then with 2-chloropyridine hydrochloride (4.1 g, 27.33 mmol). Then the mixture was heated at 80° C. overnight. After cooling, the reaction was carefully quenched with water (5 mL) and then diluted with more water (20 mL) and extracted with ethyl acetate (30 mL). The organic solution was washed with satd sodium bicarbonate, dried (MgSO4) and evaporated to give 1-t-butoxycarbonyl-4-(2-pyridoxy)piperidine (4.96 g, 72%).

Workup

  1. temperatureAfter cooling
  2. customthe reaction was carefully quenched with water (5 mL)
  3. additiondiluted with more water (20 mL)
  4. extractionextracted with ethyl acetate (30 mL)
  5. washThe organic solution was washed with satd sodium bicarbonate
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-834c236229164b4fa22338a68a43d879
Source dataset
uspto-grants-2005_04
Patent number
US06878725B2

Reaction notes

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