Convenient method for the synthesis of N-alkyl-substituted 4-hydroxy-1,2,3,4-tetrahydroisoquinolines
Title compds. I [R = alkyl, propargyl, (un)substituted benzyl] and II (R = Me, CH2Ph, CH2C6H4Cl-2) were prepd., usually in >=50% yield, by successive treatment of alkoxy-substituted N-alkylbenzylamines with BrCH2CH(OEt)2 and HCl. [on SciFinder (R)]
1990
1
50
51
CAN 113:58990
28-5
Heterocyclic Compounds (More Than One Hetero Atom)
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
5779-99-7 Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with benzylamine); 100-46-9 (Benzenemethanamine) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with methoxy(methylenedioxy)benzaldehyde); 108261-07-0P; 110103-24-7P; 128373-02-4P; 128373-03-5P; 128373-04-6P; 128373-05-7P; 128373-06-8P; 128373-07-9P; 128373-08-0P; 128373-09-1P; 128373-10-4P; 128373-11-5P; 128398-58-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 2032-35-1 (Bromoacetaldehyde diethyl acetal) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with alkoxyalkylbenzylamines)
REVIEWED
EPFL