3-Methyl-12-phenyl-1-aza-1,5,9-cyclododecatriene → 3-Methyl-12-phenyl-1-aza-cyclododecene

HRID 1154074Notes

Reaction equation

HRID 1154074 reaction equation
[CH3:1][CH:2]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH:8]=[CH:7][CH2:6][CH:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]=[CH:3]1>C1CCCCC1.[Rh].[O-2].[Al+3].[O-2].[O-2].[Al+3]>[CH3:1][CH:2]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:4]=[CH:3]1

Participants

4

Reactant 1

HCID 537330893-Methyl-12-phenyl-1-aza-1,5,9-cyclododecatriene

Product 1

HCID 204361213-Methyl-12-phenyl-1-aza-cyclododeceneYield 94%

Reagents, catalysts & solvents 2

HCID 131712135Rhodium aluminium oxideCatalystHCID 8078CyclohexaneSolvent

Procedure

253 g (1 mol) of 3-methyl-12-phenyl-1-aza-1,5,9-cyclododecatriene is dissolved in 2 liters of cyclohexane, and the solution is hydrogenated at 20°-25° C. under an initial pressure of 100 bars, in the presence of 40 g of rhodium/aluminium oxide, for 4 hours in a steel autoclave. After distilling off the solvent, there is obtained as the main fraction 242 g (0.94 mol) of 3-methyl-12-phenyl-1-aza-cyclododecene as a cis-trans isomeric mixture; b.p. 112° C./4 Pa.

Workup

  1. customis hydrogenated at 20°-25° C.
  2. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-90802776e7a84f36a36acd4ef81176b1
Source dataset
uspto-grants-1984_12
Patent number
US04487947

Reaction notes

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