Ammonia → 2-(3-Aminopropyl)-cyclohexylamine

HRID 2255290Notes

Reaction equation

HRID 2255290 reaction equation
[C:1]([CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=O)#[N:2].[NH3:12].[H][H]>[O-2].[O-2].[Ti+4]>[NH2:2][CH2:1][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[NH2:12].[NH:2]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:1]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962232-OxocyclohexanepropiononitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 92911DecahydroquinolineYield 4.5%HCID 108881552-(3-Aminopropyl)-cyclohexylamineYield 92.5%

Reagents, catalysts & solvents 1

HCID 162651Titanium oxide (Ti3O)Catalyst

Procedure

Through a tubular reactor (diameter 16 mm, packing height 50 cm, oil-heated double jacket), installed upstream of the hydrogenation reactor and packed with 63.5 g (100 ml) of titanium dioxide (anatase) in the form of 1.5 mm extrudates, there were passed upwardly, per hour, 16.0 g of 2-(2-cyanoethyl)-cyclohexanone (purity 97.5%, 0.103 mole) and 51 g of liquid ammonia (87 ml, 3.0 moles) at a pressure of 250 bar and a temperature of 80° C. Hydrogen was then added to the stream at ar ate of 60 standard liters 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 130° C. The effluent was depressurized to standard pressure, and the ammonia was distilled off. Gas-chromatographic analysis of the hydrogenation product gave 92.5% of 2-(3-aminopropyl)-cyclohexylamine and 4.5% of decahydroquinoline. The effluent was collected over a period of 46 hours and fractionated by distillation in a 30 cm packed column containing 3 mm glass rings. There were obtained 674 g of 2-(3-aminopropyl)-cyclohexylamine, corresponding to a yield of 91.0% of theory.

Workup

  1. temperatureThrough a tubular reactor (diameter 16 mm, packing height 50 cm, oil-heated double jacket)
  2. waitwere passed upwardly, per hour
  3. customa temperature of 80° 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 130° C
  6. distillationthe ammonia was distilled off

Sources & evidence

ORD record
ord-b16391fe0a5b4ccfa74f73ad9fa7cbe1
Source dataset
uspto-grants-1993_08
Patent number
US05239120

Reaction notes

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