Benzyl Bromide → 1-benzyl-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,2,3,4-tetrahydroquinoline (0.5 g, 3.75 mmol), benzyl bromide (0.67 mL, 5.63 mmol) and diisopropylethyl amine (0.98 mL, 5.63 mmol) in DMF (5 mL) was heated in an oil bath (T˜120° C.) for 16 hours. Reaction mixture was cooled, added to brine (75 mL) and extracted with ethyl acetate (100 mL). Organic layer was washed with brine (4×) and decolorized with activated charcoal. Upon filtering, it was dried with MgSO4, filtered again and evaporated to dryness to provide Compound 5 as an oily residue (420 mg) with the structure given below:

Provenance & Evidence