2,4,6-Triethylbenzene-1,3-diamine → HCID 14573496, compound

HRID 231918Notes

Reaction equation

HRID 231918 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH3:9])=[CH:6][C:5]([CH2:10][CH3:11])=[C:4]([NH2:12])[C:3]=1[CH2:13][CH3:14].CC(C)([O-])C.[K+].[H][H]>[Ru].C(O)(C)(C)C>[NH2:1][CH:2]1[CH:7]([CH2:8][CH3:9])[CH2:6][CH:5]([CH2:10][CH3:11])[CH:4]([NH2:12])[CH:3]1[CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 140941682,4,6-Triethylbenzene-1,3-diamineHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 14573496HCID 14573496, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 6386tert-ButanolSolvent

Procedure

A suitable autoclave was charged with 1 g (0.052 mol) of purified 1,3-diamino-2,4,6-triethylbenzene, 0.15 g (1.2 mmol) of potassium t-butoxide, 1.0 g of 5% Ru on alumina, and 50 mL of t-butanol and heated to 190° C. at 25.5 MPa hydrogen for 17 hours. The autoclave 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 1 mm Hg/187°-191° C. to give 6.8 g (66%) of 1,3-diamino-2,4,6-triethylcyclohexane.

Workup

  1. temperatureThe autoclave 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

Sources & evidence

ORD record
ord-c5e9b2451b3243deacf47529e9841e95
Source dataset
uspto-grants-1989_07
Patent number
US04849544

Reaction notes

Loading…