Sodium Sulfate → 2,2-Dimethyl-5-(sec-butylamino)-3-hexanone

HRID 888557Notes

Reaction equation

HRID 888557 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]([NH2:22])([CH2:20][CH3:21])[CH3:19]>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:10])([C:4](=[O:9])[CH2:5][CH:6]([NH:22][CH:18]([CH2:20][CH3:21])[CH3:19])[CH3:7])[CH3:3]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 24874Sec-ButylamineHCID 817415,5-Dimethylhexane-2,4-dione

Product 1

HCID 866247732,2-Dimethyl-5-(sec-butylamino)-3-hexanoneYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5.00 g (35.16 mmol) 2,2-dimethyl-3,5-hexanedione in 20 mL of toluene loaded with 10.00 g of sodium sulfate was added 5.14 g (70.32 mmol) sec-butylamine. The mixture was refluxed 3 days. 4.90 g of light yellow oil was obtained after work-up. The isolated yield was 71%. 1H NMR (500 MHz, C6D6): δ=11.52 (s, 1H), 5.18 (s, 1H), 2.95 (m, 1H), 1.51 (s, 3H), 1.31 (s, 9H), 1.14 (s, 2H), 0.80 (d, 3H), 0.67 (t, 3H).

Workup

  1. temperatureThe mixture was refluxed 3 days

Sources & evidence

ORD record
ord-bdfb4d6a5e784dcc8d0b2e11fee07336
Source dataset
uspto-grants-2012_08
Patent number
US08247617B2

Reaction notes

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