Homoveratrylamine → HCID 21406686, compound

HRID 1706137Notes

Reaction equation

HRID 1706137 reaction equation
[CH2:1]([NH2:13])[CH2:2][C:3]1[CH:12]=[CH:11][C:8]([O:9][CH3:10])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH:17]1[O:19][CH2:18]1>C1C=CC=CC=1.CCCCCC>[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH:17]([OH:19])[CH2:18][NH:13][CH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:8]([O:9][CH3:10])=[C:5]([O:6][CH3:7])[CH:4]=1

Participants

5

Reactant 2

HCID 8421HomoveratrylamineHCID 1510422-(2-Methylphenyl)oxirane

Product 1

HCID 21406686HCID 21406686, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

Homoveratrylamine (13.6 g, 0.0753 mole) and o-methylstyrene oxide (10.1 g, 0.0753 mole) were stirred at 100° under argon for 16 hours and then diluted with benzene and hexane and cooled in ice. The solid which precipitated was filtered and recrystallized from benzene-hexane to give 8.6 g (36%) of 2-methyl-α-[N-(3,4-dimethoxyphenethyl)aminomethyl]benzyl alcohol, mp 91°-94°.

Workup

  1. temperaturecooled in ice
  2. customThe solid which precipitated
  3. filtrationwas filtered
  4. customrecrystallized from benzene-hexane

Sources & evidence

ORD record
ord-5c415cad2e7840bb85063f0e28349eb6
Source dataset
uspto-grants-1980_06
Patent number
US04206210

Reaction notes

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