1-Phenethylamine → 2,2-dimethoxy-N-(1-phenylethyl)ethanamine

HRID 494204Notes

Reaction equation

HRID 494204 reaction equation
[CH3:1][CH:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:10][O:11][CH:12]([O:15][CH3:16])[CH2:13]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[CH3:10][O:11][CH:12]([O:15][CH3:16])[CH2:13][NH:9][CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:1]

Participants

6

Reactant 4

HCID 74081-PhenethylamineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 606869992,2-dimethoxy-N-(1-phenylethyl)ethanamineYield 69.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of α-methylbenzylamine (8.37 g, 0.069 mol) and bromoacetaldehyde dimethylacetal (11.67 g, 0.069 mol) in acetonitrile (150 ml) containing potassium carbonate (12.39 g, 0.09 mol) was heated at reflux for 2 days then cooled. The resulting precipitate was filtered off and the filtrate was concentrated in vacuo to give the crude product as an oil. Chromatography on silica gel eluting with ethyl acetate afforded the title compound as an oil (10.1 g). 1H NMR (400 MHz, CDCl3) δ(ppm): 7.31 (m, 3H), 7.23 (m, 2H), 4.43 (t, 1H), 3.75 (q, 1H), 3.35 (s, 3H), 3.31 (s, 3H), 2.63 (dd, 1H), 2.55 (dd, 1H), 1.36 (d, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. temperaturethen cooled
  4. filtrationThe resulting precipitate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give the crude product as an oil

Sources & evidence

ORD record
ord-ee264e70c716444e8f2bfa71f3b76222
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

Loading…