Aluminum(III) Chloride → 1,8-Dimethyl-1,2,3,4-tetrahydroisoquinoline
Reaction equation
Cl.Br[CH2:3][CH2:4][NH:5][CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[CH3:7].[Cl-].[Al+3].[Cl-].[Cl-]>C1C2C(CCCC2)CCC1>[CH3:7][CH:6]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[CH2:3][CH2:4][NH:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixed solution of 14.7 g of the compound (45.5 mM) prepared in Step 4 above and 100 ml of decaline, was added aluminium chloride and reacted at 140°-150° C. for 1.5 hours, which was cooled to 0° C. The reaction mixture was diluted by pouring into ice water and washed with ethyl ether. The reaction mixture was basified by adding aqueous NaOH solution and the solids produced were filtered. The filtrate was extracted from ethyl ether and the extracts was dried over anhydrous sodium sulfate, concentrated under a reduced pressure, to give 3.16 g of the title compound.