Isopropylamine → 2,2-Dimethyl-5-(iso-propylamino)-3-hexanone

HRID 888556Notes

Reaction equation

HRID 888556 reaction equation
[CH3:1][C:2]([CH3:10])([C:4](=[O:9])[CH2:5][C:6](=O)[CH3:7])[CH3:3].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH:18]([NH2:21])([CH3:20])[CH3:19]>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:10])([C:4](=[O:9])[CH2:5][CH:6]([NH:21][CH:18]([CH3:20])[CH3:19])[CH3:7])[CH3:3]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 24436Sodium SulfateHCID 817415,5-Dimethylhexane-2,4-dione

Product 1

HCID 866247722,2-Dimethyl-5-(iso-propylamino)-3-hexanoneYield 84.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 15.00 g (105.49 mmol) 2,2-dimethyl-3,5-hexanedione in 50 mL of toluene loaded with 30.00 g sodium sulfate was added 12.47 g (210.97 mmol) isopropylamine. The mixture was refluxed for 4 days. Removal of toluene resulted in a yellow oil, which was subjected to vacuum transfer at 80° C. under 125 mTorr. 16.5 g of clear oil was obtained with a yield of 84%. 1H NMR (500 MHz, C6D6): δ=11.50 (s, 1H), 5.16 (s, 1H), 3.11 (m, 1H), 1.49 (s, 3H), 1.31 (s, 9H), 0.79 (d, 6H).

Workup

  1. temperatureThe mixture was refluxed for 4 days
  2. customRemoval of toluene
  3. customresulted in a yellow oil, which
  4. customwas subjected to vacuum transfer at 80° C. under 125

Sources & evidence

ORD record
ord-7443273c353f4974909411d8d8433d56
Source dataset
uspto-grants-2012_08
Patent number
US08247617B2

Reaction notes

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