Methyl iodide → HCID 25023852, compound

HRID 888007Notes

Reaction equation

HRID 888007 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1.[C:23](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][N:19]([CH3:23])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 16225584N-(2-Aminophenyl)-4-piperidin-4-ylbenzamide

Product 1

HCID 25023852HCID 25023852, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-(2-Aminophenyl)-4-piperidin-4-ylbenzamide (Example 5, 48 mg, 0.16 mmol) was stirred and dissolved in anhydrous DMF (2 ml) at ambient temperature. Potassium carbonate (23 mg, 0.16 mmol) was added followed by iodomethane (0.01 ml, 0.16 mmol) and the mixture stirred for 3 hours. The reaction mixture was diluted with water (20 ml) and extracted with ethyl acetate. The combined extracts were washed once with brine, dried over magnesium sulfate, filtered and the solvent evaporated to give the title compound as a colourless solid (16 mg, 32%); NMR Spectrum: (DMSO-d6) 1.70 (m, 4H), 1.96 (m, 2H), 2.18 (s, 3H), 2.85 (m, 2H), 3.03 (m, 1H), 4.84 (b, 2H), 6.57 (m, 1H), 6.76 (d, 1H), 6.95 (m, 1H), 7.16 (d, 1H), 7.36 (d, 2H), 7.99 (d, 2H), 9.54 (b, 1H); Mass Spectrum: M+H+ 310.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed once with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-36692d66bfea4081b74d5441fcb2f3fb
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

Loading…