Methyl iodide → N-methyl-N-(1-(4-nitrophenyl)piperidin-4-yl)acetamide

HRID 57554Notes

Reaction equation

HRID 57554 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:19])[CH3:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].I[CH3:23].[NH4+].[Cl-]>C1COCC1>[CH3:23][N:16]([CH:13]1[CH2:12][CH2:11][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:15][CH2:14]1)[C:17](=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 49431107N-(1-(4-nitrophenyl)piperidin-4-yl)acetamide

Product 1

HCID 60301838N-methyl-N-(1-(4-nitrophenyl)piperidin-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of N-(1-(4-nitrophenyl)piperidin-4-yl)acetamide (568 mg, 2 mmol) in THF (15 mL) was added NaH (60%, 200 mg, 5 mmol) at room temperature. The reaction was stirred at 20° C. for 15 minutes. After that, iodomethane (300 mg, 4 mmol) was dropped into the reaction and stirred at 60° C. for 18 hours. The reaction was treated with sat. NH4Cl solution and extracted with n-BuOH, washed with brine, dried over Na2SO4 and concentrated to give yellow solid. MS (m/z): 278 (M+H)+

Workup

  1. stirringstirred at 60° C. for 18 hours
  2. extractionextracted with n-BuOH
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give yellow solid

Sources & evidence

ORD record
ord-3760e58dc1674a76bc78be6b5e0e1846
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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