Acetone → HCID 21434879, compound

HRID 2398187Notes

Reaction equation

HRID 2398187 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([N+:23]([O-])=O)([CH3:22])[CH3:21])=[CH:15][CH:14]=2)([CH3:12])[CH3:11])=[CH:6][CH:5]=1)([O-])=O.[N+](C1C=CC=CC=1)([O-])=O.CC(C)([N+]([O-])=O)CC1C=CC=CC=1.CC(C)=O>O1CCOCC1.[Ru]>[NH2:1][CH:4]1[CH2:5][CH2:6][CH:7]([C:10]([CH:13]2[CH2:14][CH2:15][CH:16]([CH2:19][C:20]([NH2:23])([CH3:22])[CH3:21])[CH2:17][CH2:18]2)([CH3:12])[CH3:11])[CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 7416NitrobenzeneHCID 30807782-Methyl-2-nitro-1-phenylpropaneHCID 54491284HCID 54491284, compound

Product 1

HCID 21434879HCID 21434879, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Four grams of 2[ 4-nitrophenyl]-2-[4-(2-nitro-2-methylpropyl)phenyl]propane, prepared from the condensation reaction of nitrobenzene and 1,1-dimethyl-1-nitro-2-phenylethane with acetone, dissolved in 50 ml of dioxane, was hydrogenated at 150° C. and 1400 p.s.i.g. for 5 hours in the presence of 0.55 gram of 10% ruthenium on carbon. The reaction mixture was filtered, and the filtrate was fractionally distilled to produce 2.9 grams of 2[4-aminocyclohexyl]-2-[4-(2-amino-2-methylpropyl)cyclohexyl]propane (boiling point 98° C. at 0.55 mm Hg).

Workup

  1. customwas hydrogenated at 150° C.
  2. filtrationThe reaction mixture was filtered
  3. distillationthe filtrate was fractionally distilled

Sources & evidence

ORD record
ord-9b40c78a035448b3b0a9d46a468eb948
Source dataset
uspto-grants-1977_05
Patent number
US04024185

Reaction notes

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