Homoveratrylamine → 2-Chloro-4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-6-(2-[3,4-dimethoxyphenyl]ethylamino)-1,3,5-triazine

HRID 1735130Notes

Reaction equation

HRID 1735130 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[CH:15]=3)C2)[N:3]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:33][CH2:34][NH2:35])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32].O1CCOC[CH2:37]1>C(=O)([O-])[O-].[Na+].[Na+]>[Cl:1][C:2]1[N:7]=[C:6]([N:35]2[CH2:34][CH2:33][C:27]3[C:28](=[CH:29][C:30]([O:31][CH3:32])=[C:25]([O:24][CH3:23])[CH:26]=3)[CH2:37]2)[N:5]=[C:4]([NH:9][CH2:18][CH2:17][C:16]2[CH:11]=[CH:12][C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[CH:15]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8421HomoveratrylamineHCID 312751,4-DioxaneHCID 194368602,4-Dichloro-6-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-l,3,5-triazine

Product 1

HCID 194368472-Chloro-4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-6-(2-[3,4-dimethoxyphenyl]ethylamino)-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

2,4-Dichloro-6-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-l,3,5-triazine (3.08 g, 9.03 mM) in dioxane (50 mL) and aqueous sodium carbonate solution (50 mL, 10% solution) was treated with 2-(3,4-dimethoxyphenyl)ethylamine (1.64 g, 9.03 mM). After stirring 18 hrs at ambient temperature the mixture was extracted with methylene chloride (3×75 mL). Filtration through a cotton plug and concentration provided a solid which was recrystallized from methylene chloride/ethanol to provide 3.52 g, (80%), mp=152°-153° C.

Workup

  1. extractionwas extracted with methylene chloride (3×75 mL)
  2. filtrationFiltration
  3. concentrationthrough a cotton plug and concentration
  4. customprovided a solid which
  5. customwas recrystallized from methylene chloride/ethanol
  6. customto provide 3.52 g, (80%), mp=152°-153° C.

Sources & evidence

ORD record
ord-d683af7d7d5a450c8c2d572d88f05b64
Source dataset
uspto-grants-1996_07
Patent number
US05536722

Reaction notes

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