反应详情

3-(13-Bromo-tridecyl)-pyridine (1 mmol) was added to 5,6,7,8-tetrahydro-isoquinoline (5 ml), and the mixture was heated at 50 C overnight. The resulting residue was treated with ether, and the ether was decanted after deposition for 30′. The residue was partitioned between water and ether. The aqueous layer was washed extensively with ether, and then the aqueous layer was extracted with chloroform. The chloroform was removed to afford the product (62%). 1HNMR (300 MHz, CDCl3, ppm), 9.22 (s, 1H), 8.90 (d, J=6.3, 1H), 8.44 (br, 2H), 7.67 (d, J=6.3, 1H), 7.55 (d, 8.1, 7.24-7.28 (m, 1H), 4.83 (t, J=7.2, 2.98-3.01 (m, 4H), 2.60 (t, J=7.8, 2H), 1.94-2.02 (m, 2H), 1.87-1.90 (m, 4H), 1.56-1.60 (m, 2H), 1.19-1.35 (br, 20H); 13CNMR, 157.87, 148.79, 146.13, 144.20, 140.68, 138.95, 138.80, 137.26, 128.08, 123.92, 61.40, 58.62, 33.30, 32.20, 31.34, 29.94, 29.82, 29.77, 29.67, 29.42, 29.36, 26.71, 26.46, 21.40, 18.81.

1. temperaturethe mixture was heated at 50 C overnight
2. customthe ether was decanted after deposition for 30′
3. customThe residue was partitioned between water and ether
4. washThe aqueous layer was washed extensively with ether
5. extractionthe aqueous layer was extracted with chloroform
6. customThe chloroform was removed