Pentamethyldiethylenetriamine → HCID 57939118, compound

HRID 1436354Notes

Reaction equation

HRID 1436354 reaction equation
[CH2:1]([C:3]1([CH3:15])[CH:8]([CH3:9])[C:7](=[O:10])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[N:4]1[OH:14])[CH3:2].CN(C)CCN(C)CCN(C)C.Br[CH:29]([CH3:40])[C:30]([O:32][CH2:33][CH2:34][O:35][C:36](=[O:39])[CH:37]=[CH2:38])=[O:31]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1([CH3:15])[CH:8]([CH3:9])[CH:7]([OH:10])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[N:4]1[O:14][CH:37]([CH3:38])[C:36]([O:35][CH2:34][CH2:33][O:32][C:30](=[O:31])[CH:29]=[CH2:40])=[O:39])[CH3:2]

Participants

5

Reactant 3

HCID 18196PentamethyldiethylenetriamineHCID 101311892-Propenoic acid, 2-(2-bromo-1-oxopropoxy)ethyl esterHCID 18448689HCID 18448689, compound

Product 1

HCID 57939118HCID 57939118, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
10 °C

Procedure

To a stirred solution of 99.6 g (0.46 mol) of 2,6-diethyl-1-hydroxy-2,3,6-trimethyl-piperidin-4-one (prepared as described in U.S. Pat. No. 6,353,107 B1, example 2), 66.3 g (0.46 mol) of CuBr and 29.4 g (0.46 mol) Cupper in 1000 ml toluene 160 g (0.92 mol) of N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDTA) are added. The brown suspension is then cooled to 10° C. and 116 g (0.46 mol) of acrylic acid 2-(2-bromo-propionyloxy)-ethyl ester dissolved in 250 ml toluene are added dropwise while keeping the temperature below 15° C. The reaction mixture is stirred for another 12 h at room temperature and then filtered. The filtrate is washed with water (3×500 ml), then with a 10% solution of EDTA (3×500 ml), dried over NaSO4 and evaporated. The residue is chromatographed over Silica gel with hexane-ether (7:3) to afford 165 g of the title compound as slightly yellow oil.

Workup

  1. additionare added dropwise
  2. customthe temperature below 15° C
  3. filtrationfiltered
  4. washThe filtrate is washed with water (3×500 ml)
  5. dry with materialwith a 10% solution of EDTA (3×500 ml), dried over NaSO4
  6. customevaporated
  7. customThe residue is chromatographed over Silica gel with hexane-ether (7:3)

Sources & evidence

ORD record
ord-6bcd4138d93e47c8bcdaf288e44b102f
Source dataset
uspto-grants-2009_11
Patent number
US07619050B2

Reaction notes

Loading…