Styrene Oxide → T6668830

HRID 893323Notes

Reaction equation

HRID 893323 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH2:7].[CH2:13]1[O:21][CH:14]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH:7][CH2:13][CH:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7276Styrene OxideHCID 79832Veratrylamine

Product 1

HCID 4719987T6668830Yield 46.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Heat a solution of 3,4-dimethoxybenzylamine (16.7 g) and styrene oxide (12.0 g) in acetonitrile (250 mL) at reflux for 16 h. Concentrate to a residue and distill the residue, collecting the fraction distilling above 120° C. (0.5 mm). Recrystallize the solidified distillate from benzene/hexane to give N-(3,4-dimethoxybenzyl)-2-hydroxy-2-phenylethylamine (13.4 g), mp=93°-94° C.

Workup

  1. temperatureat reflux for 16 h
  2. concentrationConcentrate to a residue
  3. distillationdistill the residue
  4. customcollecting the fraction
  5. distillationdistilling above 120° C. (0.5 mm)
  6. customRecrystallize the solidified distillate from benzene/hexane

Sources & evidence

ORD record
ord-ab45bb94c8cc49eb9720fccebb2167fb
Source dataset
uspto-grants-1992_06
Patent number
US05124337

Reaction notes

Loading…