Water → N-(1-(4-nitrophenyl)piperidin-4-yl)acetamide

HRID 57553Notes

Reaction equation

HRID 57553 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:10])[CH3:9])[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.O>CN(C=O)C>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([N:1]2[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:10])[CH3:9])[CH2:3][CH2:2]2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 14451564-Acetamidopiperidine

Product 1

HCID 49431107N-(1-(4-nitrophenyl)piperidin-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(piperidin-4-yl)acetamide (341 mg, 2.4 mmol) in DMF (15 mL) was added K2CO3 (331 mg, 2.4 mmol) and 1-fluoro-4-nitrobenzene (282 mg, 2 mmol) at room temperature. The reaction was stirred at 80° C. for 24 hours. After that, the reaction was poured into 50 mL of water and extracted with EA (3×25 mL), washed with H2O (25 mL) and brine (25 mL), dried over Na2SO4 and concentrated to give yellow solid. MS (m/z): 264 (M+H)+

Workup

  1. extractionextracted with EA (3×25 mL)
  2. washwashed with H2O (25 mL) and brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give yellow solid

Sources & evidence

ORD record
ord-018ba99780cb40a7b7f50a5ee3b71d5d
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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