Ammonia → Indolizidine

Through a tubular reactor (diameter 16 mm, packing height 50 cm, oil-heated double jacket), installed up-stream of the hydrogenation reactor and packed with 67.2 g (96 ml) of γ-aluminum oxide in the form of 1.5 mm extrudates, there were pumped upwardly, per hour, 11.0 g of 2-(2-cyanoethyl)-cyclopentanone (purity 77.0%, 0.062 mole) and 535 ml of liquid ammonia (321 g, 18.9 moles) at a pressure of 250 bar and a temperature of 70° C. Hydrogen was then added to the stream at a rate of 60 standard liters (2.7 moles) per hour, and the effluent from the in-line imination reactor was passed upwardly through the hydrogenation reactor at a pressure of 250 bar and a temperature of 120° C. The product obtained after an on-stream period of 45.4 hours was worked up by fractional distillation. There were obtained 91.2 g of 1-azabicyclo[4.3.0]nonane (b.p.=80° C./ 50 mm Hg) and 224.4 g of 2-(3-aminopropyl)-cyclopentylamine (b.p.=122° C./28 mm Hg)l. The yield of 2-(3-aminopropyl)-cyclopentylamine was 56.3% of theory.

1. temperatureThrough a tubular reactor (diameter 16 mm, packing height 50 cm, oil-heated double jacket)
2. waitwere pumped upwardly, per hour
3. customa temperature of 70° C
4. customthe effluent from the in-line imination reactor was passed upwardly through the hydrogenation reactor at a pressure of 250 bar
5. customa temperature of 120° C
6. customThe product obtained after an on-stream period of 45.4 hours
7. distillationwas worked up by fractional distillation

ORD record

ord-5873bb702e564bb898f6d8f82dc59ee6

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05239120