Water → 1-(4-nitro-3-(2-(piperidin-1-yl)ethoxy)phenyl)pyridin-2(1H)-one

HRID 1802644Notes

Reaction equation

HRID 1802644 reaction equation
F[C:2]1[CH:3]=[C:4]([N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[O:17])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[N:18]1([CH2:24][CH2:25][OH:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[H-].[Na+].O>C1COCC1.CCOC(C)=O>[N+:8]([C:7]1[CH:6]=[CH:5][C:4]([N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[O:17])=[CH:3][C:2]=1[O:26][CH2:25][CH2:24][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 18232N-Piperidinoethanol2×HCID 24758Sodium hydride2×HCID 589627441-(3-fluoro-4-nitro-phenyl)-1H-pyridin-2-one

Product 1

HCID 669741821-(4-nitro-3-(2-(piperidin-1-yl)ethoxy)phenyl)pyridin-2(1H)-oneYield 72.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-(3-fluoro-4-nitrophenyl)pyridin-2(1H)-one (0.70 g, 2.99 mmol) in anhydrous THF (6 mL) at room temperature, a pre-mixed solution of 1-piperidineethanol (0.40 mL, 3.02 mmol) and NaH (60%, 157 mg, 3.92 mmol) in anhydrous THF (8 mL) was added. After addition, the suspension became clear. The mixture was stirred at room temperature overnight. HPLC showed that the reaction was incomplete. Another pre-mixed solution of 1-piperidineethanol (0.40 mL, 3.02 mmol) and NaH (60%, 157 mg, 3.92 mmol) in anhydrous THF (5 mL) was added. After 1 h of stirring, the reaction was completed. H2O and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 1-(4-nitro-3-(2-(piperidin-1-yl)ethoxy)phenyl)pyridin-2(1H)-one (0.74 g).

Workup

  1. additionAfter addition
  2. stirringAfter 1 h of stirring
  3. customThe organic phase was separated
  4. washwashed with 5% NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfda8be3a5414479b69e5551ab00d878
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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