Ammonia → Decahydroquinoline

HRID 2255288

Reaction equation

HRID 2255288 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]>>[NH:2]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:1]1.[NH2:2][CH2:1][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[NH2:12]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962232-OxocyclohexanepropiononitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 92911DecahydroquinolineHCID 108881552-(3-Aminopropyl)-cyclohexylamine

Procedure

Example 3 was repeated except that 29.7 g of 2-(2-cyanoethyl)-cyclohexanone (purity 96%, 0.189 mole) and 1,200 ml of liquid ammonia (720 g, 42.4 moles) were passed upwardly through the first reactor, per hour, at a pressure of 250 bar and a temperature of 70° C. Hydrogen was then added to the stream at a rate of 125 standard liters (5.6 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 125° C. After an on-stream time of 17.8 hours the separation and distillation measures as per Example 2 had yielded, besides 66.4 g of decahydroquinoline, 365 g of 2-(3-aminopropyl)-cyclohexylamine. The yield of 2-(3-aminopropyl)-cyclohexylamine was 69.7% of theory.

Workup

  1. waitwere passed upwardly through the first reactor, per hour, at a pressure of 250 bar
  2. customa temperature of 70° C
  3. customthe effluent from the in-line imination reactor was passed upwardly through the hydrogenation reactor at a pressure of 250 bar
  4. customa temperature of 125° C
  5. customAfter an on-stream time of 17.8 hours the separation and distillation measures as per Example 2

Sources & evidence

ORD record
ord-195beb4eb06445c9bcedf13269f10ea4
Source dataset
uspto-grants-1993_08
Patent number
US05239120

Linked notes

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