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

HRID 559478Notes

Reaction equation

HRID 559478 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)ethanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of α-methylbenzylamine (8.37 g, 0.07 mol) and bromoacetaldehyde dimethylacetal (11.67 g, 0.07 mol) in acetonitrile (150 ml) containing potassium carbonate (12.39 g, 0.09 mol) was heated at reflux for 2d and cooled. The solid was filtered off and the filtrate was concentrated under reduced pressure to leave an oil. Chromatography on silica gel eluting with ethyl acetate afforded the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperaturecooled
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto leave an oil

Sources & evidence

ORD record
ord-90d77be095904265a7d0f9d7294cb682
Source dataset
uspto-grants-2011_11
Patent number
US08063078B2

Reaction notes

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