Hexamethylenetetramine → 3,4-Dihydro-6,7-dimethoxyisoquinoline

HRID 38310

Reaction equation

HRID 38310 reaction equation
[C:1](O)(=O)C.FC(F)(F)C(O)=O.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:22][CH2:23][NH2:24])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C1N2CN3CN(C2)CN1C3>O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[CH:1]=[N:24][CH2:23][CH2:22]2

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 8421HomoveratrylamineHCID 23437676Trifluoroacetic acid acetate

Product 1

HCID 300583,4-Dihydro-6,7-dimethoxyisoquinolineYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic acid/trifluoroacetic acid (100 mL) was added to a solution of 2-(3,4-dimethoxyphenyl)ethanamine (20 g, 110.38 mmol, 1.00 equiv) and hexamethylenetetramine (31 g, 221.11 mmol, 2.00 equiv). The resulting solution was heated at reflux for about 5 hours in an oil bath. After adding water (100 mL), the solution was extracted with dichloromethane (3×200 mL), and the organic layers were combined and dried over anhydrous sodium sulfate. Solids were removed by filtration, and the resulting filtrate was concentrated in vacuo to give the title product as a yellow oil (20 g, yield=95%). LC-MS: m/z=192 (MH)+.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for about 5 hours in an oil bath
  3. extractionthe solution was extracted with dichloromethane (3×200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSolids were removed by filtration
  6. concentrationthe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ee60041f966b45bd8141886f41499c14
Source dataset
uspto-grants-2013_09
Patent number
US08524733B2

Linked notes

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