Methyl iodide → N-benzyl-N-methyl-1-(1-methyl-1H-indole-2-carbonyl)piperidine-4-carboxamide

HRID 83640Notes

Reaction equation

HRID 83640 reaction equation
[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:32]>C1COCC1.O>[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]([CH3:32])[C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66571403N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

Product 1

HCID 66571404N-benzyl-N-methyl-1-(1-methyl-1H-indole-2-carbonyl)piperidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (100 mg, 0.266 mmol) was added to a suspension of sodium hydride (12.78 mg, 0.320 mmol) in THF (Volume: 1.5 mL) at 0° C. The reaction was stirred for 10 minutes before iodomethane (0.200 mL, 3.20 mmol) was added. The reaction was allowed to stir at room temperature overnight. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution. It was dried over magnesium sulfate, filtered and concentrated. The crude material was purified using 50%-100% ethyl acetate in hexanes. (Yield: 41.5 mg, white solid) To obtain white solid as a product. 1H-NMR (400 MHz, DMSO-d6) 7.63-7.57, 7.53-7.47, 7.43-7.16, 7.13-7.05, 6.63, 4.67, 4.58-4.00, 3.78-3.71, 3.21-2.91, 2.79, 1.87-1.52

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialIt was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified
  8. custom(Yield: 41.5 mg, white solid) To obtain white solid as a product

Sources & evidence

ORD record
ord-fef3bfbd87c74a87b30ebe3910111b2a
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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