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

HRID 23951

Reaction equation

HRID 23951 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 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 sat. sodium bicarbonate, dried (MgSO4) and evaporated to give 1-t-butoxycarbonyl-4-(2-pyridoxy)piperidine (4.96 g 72%).

Workup

  1. temperatureAfter cooling the reaction
  2. customwas 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 sat. sodium bicarbonate
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-390aae966993417181c270dae2276020
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Linked notes

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