Ammonia → HCID 20449668, compound

HRID 647236Notes

Reaction equation

HRID 647236 reaction equation
[C:1]1([C:7]([CH3:18])([CH2:13][CH2:14][CH2:15][C:16]#[N:17])[CH2:8][CH2:9][CH2:10][C:11]#[N:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C)(C)C.N.[H][H]>[Ru].[Pd].O>[C:1]1([C:7]([CH3:18])([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6386tert-ButanolHCID 204315265-Methyl-5-phenylnonanedinitrileHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20449668HCID 20449668, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23950RutheniumCatalystHCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A one liter autoclave was charged with 50 g 0.21 mol of a dinitrile consisting essentially of 5-phenyl-5-methylnonanedinitrile. Also charged to the reactor was 300 ml 237 g t-butyl alcohol, 25 ml water, 5 g of 5 percent by weight ruthenium on alumina and 2 g of 5 percent by weight palladium on alumina. The reactor was flushed with nitrogen and charged with 70 g 4.1 mol of ammonia. The reactor was pressured to 1200 psig with hydrogen and heated with stirring at 170° C. for two hours. Hydrogen uptake indicated only reduction of nitrile groups to amino groups had taken place thus producing the aralkylenediamine, 5-phenyl-5-methyl-1,9-nonanediamine.

Workup

  1. additionAlso charged to the reactor
  2. customThe reactor was flushed with nitrogen
  3. temperatureheated

Sources & evidence

ORD record
ord-f9d854d725434f3eb7748cb2d2be0891
Source dataset
uspto-grants-1983_10
Patent number
US04408037

Reaction notes

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