Methyl iodide → HCID 22225887, compound

HRID 635917Notes

Reaction equation

HRID 635917 reaction equation
[C:1]([CH2:3][NH:4][CH2:5][CH2:6][CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)#[N:2].IC.[C:22](=O)([O-])[O-].[K+].[K+]>C(#N)C.ClCCl>[CH3:22][N:4]([CH2:5][CH2:6][CH:7]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:3][C:1]#[N:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22225891HCID 22225891, compound

Product 1

HCID 22225887HCID 22225887, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.72 g (2.9 mmol) N-cyanomethyl-3,3-diphenylpropylamine (from step 1), 0.49 g (3.4 mmol) iodomethane and 1.6 g potassium carbonate in 5 ml acetonitrile was stirred at room temperature for 16 hours. The reaction mixture was diluted with dichloromethane, washed with water, the solvent evaporated, and the residue chromatographed on silica gel column with 20% ethyl acetate in hexanes to give 0.33 g (yield 43%) N-methyl-N-cyanomethyl-3,3-diphenylpropylamine as an oil which solidified on standing. 1H NMR ((CDCl3, 300 MHz) 7.30-7.10 (m, 10 H), 4.02 (t, 1 H, 3.47 (s, 3 H), 2.38 (t, 2 H), 2.32 (s, 3H), 2.19 (dt, 2H);

Workup

  1. washwashed with water
  2. customthe solvent evaporated
  3. customthe residue chromatographed on silica gel column with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-dd9bc556e37743e2a68cb7cb81ec5281
Source dataset
uspto-grants-2001_02
Patent number
US06191165B1

Reaction notes

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