Cyanuric chloride → 2,4-Dichloro-6-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-l,3,5-triazine
Reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].Cl.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[CH2:19][NH:18][CH2:17][CH2:16]2>C(=O)([O-])O.[Na+].O>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([N:18]2[CH2:17][CH2:16][C:15]3[C:20](=[CH:21][C:22]([O:23][CH3:24])=[C:13]([O:12][CH3:11])[CH:14]=3)[CH2:19]2)[N:7]=1Participants
5
Procedure
To a 0° C. stirred slurry of cyanuric chloride (8.03 g, 43.5 mM) in saturated sodium hydrogen carbonate solution (300 mL) was added 6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline hydrochloride (10 g, 43.5 mM) in water (50 mL) at a rate that maintained the internal temperature below 8° C. After 10 min the product was extracted with methylene chloride, filtered through a cotton plug and concentrated to a solid. Filtration of a concentrated methylene chloride solution of the crude product through a 2×2 inch silica gel pad eluting with 50% ethyl acetate/hexanes provided pure product, 12.3 g, (83%).
Workup
- temperaturemaintained the internal temperature below 8° C
- extractionAfter 10 min the product was extracted with methylene chloride
- filtrationfiltered through a cotton plug
- concentrationconcentrated to a solid
- filtrationFiltration of a concentrated methylene chloride solution of the crude product through a 2×2 inch silica gel pad
- washeluting with 50% ethyl acetate/hexanes provided pure product, 12.3 g, (83%)
Sources & evidence
- ORD record
- ord-1c2887d4abbd4530a68cf37cddd9a97a
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05536722
Reaction notes
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