p-Toluenesulfonic acid → 1-(2-Benzobicyclo[2.2.1]heptenyl)piperidine

2-Benzobicyclo[2.2.1]hepteneone (0.5 g) was combined with piperidine (1 ml), p-toluenesulfonic acid (0.1 g), and toluene (25 ml) and heated to reflux for 20 hours. The solution was concentrated on a rotary evaporator and the residue was distilled on a Kugelrohr apparatus (120° C. at 0.05 mm Hg). The distillate was combined with glacial acetic acid (10 ml) and sodium cyanoborohydride (0.5 g) and stirred at room temperature for 12 hours. The solution was made basic by the addition of 10% sodium hydroxide in water. The resulting mixture was extracted with ether (3×50 ml) and the combined ether layers were dried over magnesium sulfate and concentrated on a rotary evaporator. The residue was distilled on a Kugelrohr apparatus (120° C. at 0.05 mm Hg) to provide the product as a colorless oil. Analytical data are reported in Table I.

1. temperatureheated
2. temperatureto reflux for 20 hours
3. concentrationThe solution was concentrated on a rotary evaporator
4. distillationthe residue was distilled on a Kugelrohr apparatus (120° C. at 0.05 mm Hg)
5. additionThe solution was made basic by the addition of 10% sodium hydroxide in water
6. extractionThe resulting mixture was extracted with ether (3×50 ml)
7. dry with materialthe combined ether layers were dried over magnesium sulfate
8. concentrationconcentrated on a rotary evaporator
9. distillationThe residue was distilled on a Kugelrohr apparatus (120° C. at 0.05 mm Hg)

ORD record

ord-20beecf6dd404ed0ac81ca1744e8c45c

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05089506