Triethylamine → 3-[N-methyl-N-(2-(3,4-dimethoxyphenyl)ethyl)amino]-2-methylpropionitrile

HRID 728051Notes

Reaction equation

HRID 728051 reaction equation
I.[CH3:2][NH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1.[C:16](#[N:20])[C:17]([CH3:19])=[CH2:18].C(N(CC)CC)C>ClCCl>[CH3:2][N:3]([CH2:18][CH:17]([CH3:19])[C:16]#[N:20])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31368MethacrylonitrileHCID 44144798(3,4-Dimethoxyphenethyl)(methyl)ammonium iodide

Product 1

HCID 199703153-[N-methyl-N-(2-(3,4-dimethoxyphenyl)ethyl)amino]-2-methylpropionitrileYield 39.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture comprising 6.5 g of N-methyl-2-(3,4-dimethoxyphenyl)ethylamine hydroiodide, 1.6 g of methacrylonitrile and 2.4 g of triethylamine was heated at about 70° C. for 2.5 hours and cooled, followed by the addition of dichloromethane. The obtained mixture was washed with water, dried over magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel column chromatography (solvent: dichloromethane/ethanol (100:1)) to obtain 2.1 g of 3-[N-methyl-N-(2-(3,4-dimethoxyphenyl)ethyl)-amino]-2-methylpropionitrile.

Workup

  1. temperaturecooled
  2. washThe obtained mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography (solvent: dichloromethane/ethanol (100:1))

Sources & evidence

ORD record
ord-61765b89637542e4bd93bf4173b012e6
Source dataset
uspto-grants-1991_09
Patent number
US05047417

Reaction notes

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