2-BUTYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE synthesis
- Product Name:2-BUTYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
- CAS Number:92195-34-1
- Molecular formula:C13H19N
- Molecular Weight:189.3
Yield:92195-34-1 118 mg
Reaction Conditions:
Stage #1: 2-(2-oxoethyl)benzaldehyde;n-butylamine hydrochloridewith sodium hydrogencarbonate in ethanol at 20; for 0.166667 h;
Stage #2: with sodium cyanotrihydroborate;acetic acid in ethanol at 20; for 4 h;
Steps:
General procedure for the synthesis of fluorine-containing N-heterocyclic derivatives byoxidative ring cleavage followed by ring closure with reductive amination
General procedure: NaIO4 (1.5 equiv) was added to a stirred solution of dihydroxy compounds (4 mmol) inTHF/H2O (25 mL/2 mL). After stirring for 1 h at 20 °C under Ar atmosphere, H2O was addeduntil the dissolution of the precipitate (40 mL). The mixture was then extracted with CH2Cl2 (3× 20 mL) and the combined extract was dried over Na2SO4. The crude dialdehyde product wasimmediately used for reductive ring closing without purification. Fluorinated andpolyfluorinated amines (1 equiv) and NaHCO3 (2 equiv) were added to the solution of thecorresponding diformyl intermediates in EtOH (20 mL) and the mixture was stirred at 20 °Cfor 10 min. After the addition of NaCNBH3 (1 equiv) and AcOH (2 drops), stirring was continued for another 4 h at 20 °C. The reaction mixture was diluted with H2O (20 mL) andextracted with CH2Cl2 (3 × 20 mL). The combined organic layers were dried over Na2SO4 andconcentrated under reduced pressure. The crude product was purified by columnchromatography on silica gel (n-hexane/EtOAc).
References:
ábrahámi, Renáta A.;Fustero, Santos;Fül?p, Ferenc;Kiss, Loránd [Synlett,2018,vol. 29,# 15,p. 2066 - 2070] Location in patent:supporting information
