4,6-Di(propan-2-yl)benzene-1,3-diamine → HCID 14573497, compound

HRID 231919Notes

Reaction equation

HRID 231919 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([CH:11]([CH3:13])[CH3:12])=[C:4]([NH2:14])[CH:3]=1.CC(C)([O-])C.[K+].[H][H]>[Ru].C(O)(C)(C)C>[NH2:1][CH:2]1[CH:7]([CH:8]([CH3:9])[CH3:10])[CH2:6][CH:5]([CH:11]([CH3:13])[CH3:12])[CH:4]([NH2:14])[CH2:3]1

Participants

6

Reactant 3

HCID 127021284,6-Di(propan-2-yl)benzene-1,3-diamineHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 14573497HCID 14573497, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 6386tert-ButanolSolvent

Procedure

A suitable autoclave was charged with 20.7 g (0.108 mol) of purified 1,3-diamino-4,6-diisopropylbenzene, 0.3 g (2.7 mmol) of potassium t-butoxide, 2.0 g of 5% Ru on alumina, and 100 mL of t-butanol. The autoclave was heated to 190° C. at 25.5 MPa hydrogen for 24 hours. It was then cooled and its contents filtered. The solvent was removed from the filtrate in vacuo and the resulting liquid distilled through a 20.3 cm Vigreaux column at about 4 mm Hg/115°-118° C. to give 5.9 g (28%) of 1,3-diamino-4,6-diisopropylcyclohexane.

Workup

  1. temperatureIt was then cooled
  2. filtrationits contents filtered
  3. customThe solvent was removed from the filtrate in vacuo
  4. distillationthe resulting liquid distilled through a 20.3 cm Vigreaux column at about 4 mm Hg/115°-118° C.

Sources & evidence

ORD record
ord-9ef92ffbc1fc414087c0bfcf379009cc
Source dataset
uspto-grants-1989_07
Patent number
US04849544

Reaction notes

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