6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline → HCID 23193291, compound

HRID 1376505Notes

Reaction equation

HRID 1376505 reaction equation
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[CH2:2]1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[CH2:23][NH:22][CH2:21][CH2:20]2>C(O)(C)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[CH2:23][N:22]([CH2:2][CH:3]([OH:1])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH2:21][CH2:20]2

Participants

4

Reactant 2

HCID 156236,7-Dimethoxy-1,2,3,4-TetrahydroisoquinolineHCID 213272-((4-Nitrophenoxy)methyl)oxirane

Product 1

HCID 23193291HCID 23193291, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1,2-epoxy-3-(4-nitrophenoxy)propane (4 g) and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (5.4 g) in isopropanol (100 ml) was heated under reflux for 3 h and evaporated. The residue was purified by column chromatography to give the title compound (7.6 g) as a yellow oil which solidified on standing.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customevaporated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-900a9a201c904822a4554b83c7ff98e8
Source dataset
uspto-grants-1997_09
Patent number
US05663179

Reaction notes

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