Hexane → HCID 58933201, compound

HRID 854161Notes

Reaction equation

HRID 854161 reaction equation
[CH3:1][C:2](=[N:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7].[H][H].O(C(C)C)[K].CCCCCC>C1C=CC=CC=1>[CH3:1][CH:2]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:3][CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 8058HexaneHCID 58933206HCID 58933206, compoundHCID 178418361HCID 178418361, compoundHCID 178459948HCID 178459948, compound

Product 1

HCID 58933201HCID 58933201, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of N-(1,5-dimethyl-4-hexenylidene)aniline (2.0 g) in benzene (2 ml) was added under a flow of hydrogen gas to a mixture of RuHCl(R,R—BINAP)(R,R—CYDN) (5 mg) and KOiPr (5 mg) in a Schlenk flask. The flask was then cooled to liquid nitrogen temperature, filled with H2 gas, closed and allowed to gradually warm to room temperature. The mixture was vigorously stirred for 24 hours. A 1H NMR spectrum of the reaction mixture indicated complete conversion of the imine to the amine. Hexane (10 ml) was added to the mixture, which was then eluted (hexane) through a short column of silica gel in order to remove the spent catalyst and KOiPr. Evaporation of the hexane under reduced pressure resulted in spectroscopically pure N-(1,5-dimethyl-4-hexenyl)aniline, as verified by 1H and 13C NMR.

Workup

  1. temperatureThe flask was then cooled to liquid nitrogen temperature
  2. additionfilled with H2 gas
  3. customclosed
  4. washwas then eluted (hexane) through a short column of silica gel in order
  5. customto remove the spent catalyst and KOiPr
  6. customEvaporation of the hexane under reduced pressure

Sources & evidence

ORD record
ord-0fdf55cd92db4685a00a0513d8c7bd12
Source dataset
uspto-grants-2007_08
Patent number
US07256311B2

Reaction notes

Loading…