1,2,3,4-Tetrahydroisoquinoline → 2-[4-(4-Butyl-phenyl)-butyl]-5,6,7,8-tetrahydro-isoquinolinium bromide

Participants

Reaction Steps

1-(4-Bromo-butyl)-4-butyl-benzene (1 mmol) was added to a solution of tetrahydroisoquinoline (2 mmol) in acetonitrile, and the solution was refluxed for 24 hours. The acetonitrile was removed in vacuum, and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no tetrahydroisoquinoline was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (72%). 1HNMR (300 MHz, CDCl3, ppm), 9.12 (s, 1H), 8.85 (d, J=6.0, 1H), 7.61 (d, J=6.0, 1H), 7.02-7.08 (m, 4H), 4.83 (t, 7.5, 3H), 2.92-2.94 (m, 4H), 2.61 (t, J=7.5, 2H), 2.54 (t, J=7.5, 2H), 1.90-2.04 (m, 2H), 1.80-1.90 (m, 4H), 1.62-1.69 (m, 2H), 1.53-1.62 (m, 2H), 1.29-1.37 (m, 2H), 0.90 (t, J=7.2, 3H). 13CNMR, 157.94, 144.18, 140.82, 140.64. 138.96, 138.37, 128.65, 128.48, 127.99, 61.16, 35.54, 34.99, 34.05, 31.56, 29.92, 27.98, 26.69, 22.74, 21.37, 14.33.

Provenance & Evidence