2-Nitropropane → HCID 178457349, compound

HRID 2398186Notes

Reaction equation

HRID 2398186 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([CH3:16])([CH3:15])[N+:12]([O-])=O)=[CH:6][CH:5]=1)([O-])=O.[N+](C1C=CC(CCl)=CC=1)([O-])=O.[N+](C(C)C)([O-])=O.[H-].[Li+]>O1CCOCC1.[Ru]>[NH2:1][C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][C:11]([NH2:12])([CH3:15])[CH3:16])[CH2:6][CH2:5]1.[NH2:1][C@@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][C:11]([NH2:12])([CH3:15])[CH3:16])[CH2:6][CH2:5]1

Participants

8

Reactant 4

HCID 3982-NitropropaneHCID 74824-Nitrobenzyl chlorideHCID 62714Lithium hydrideHCID 2280911-(2-methyl-2-nitropropyl)-4-nitrobenzene

Product 2

HCID 178457349HCID 178457349, compoundHCID 178457350HCID 178457350, compound

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Ten grams of 2-(4-nitrophenyl)-1,1-dimethyl-1-nitroethane, prepared from the reaction of p-nitrobenzyl chloride and 2-nitropropane catalyzed by lithium hydride, dissolved in dioxane, was hydrogenated in the presence of 0.8 grams of 10% ruthenium on carbon at 120° C. and 1600 p.s.i.g. for 7 hours. The reaction mixture was filtered and the filtrate was fractionally distilled to produce 6.7 grams of trans 2-(4-aminocyclohexyl)-1,1-dimethylethylamine (A) boiling point 78° C. at 0.2 mm Hg, and 1.5 grams of cis 2-(4-aminocyclohexyl)-1,1-dimethylethylamine (B), boiling point 69° C. at 0.2 mm Hg.

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationthe filtrate was fractionally distilled

Sources & evidence

ORD record
ord-f7689466884c423d86f787d6c5c21487
Source dataset
uspto-grants-1977_05
Patent number
US04024185

Reaction notes

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