Dimethyl diethylmalonate → Bis-(1-allyl-2,2,6,6-tetramethyl-4-piperidinyl) diethylmalonate

HRID 847669Notes

Reaction equation

HRID 847669 reaction equation
[CH2:1]([C:3]([CH2:12][CH3:13])([C:8]([O:10][CH3:11])=[O:9])[C:4]([O:6][CH3:7])=[O:5])[CH3:2].[CH2:14]([N:17]1[C:22]([CH3:24])([CH3:23])[CH2:21]C(O)[CH2:19][C:18]1([CH3:27])[CH3:26])[CH:15]=[CH2:16]>C1(C)C(C)=CC=CC=1>[CH2:12]([C:3]([CH2:1][CH3:2])([C:8]([O:10][CH:11]1[CH2:27][C:18]([CH3:19])([CH3:26])[N:17]([CH2:14][CH:15]=[CH2:16])[C:22]([CH3:21])([CH3:23])[CH2:24]1)=[O:9])[C:4]([O:6][CH:7]1[CH2:24][C:22]([CH3:23])([CH3:21])[N:17]([CH2:14][CH:15]=[CH2:16])[C:18]([CH3:27])([CH3:26])[CH2:19]1)=[O:5])[CH3:13]

Participants

4

Reactant 2

HCID 117935Dimethyl diethylmalonateHCID 129919752,2,6,6-Tetramethyl-1-(prop-2-en-1-yl)piperidin-4-ol

Product 1

HCID 20512150Bis-(1-allyl-2,2,6,6-tetramethyl-4-piperidinyl) diethylmalonate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

After the addition of 1 g of tetrabutyl-orthotitanate, 47 g of dimethyl diethylmalonate and 98.6 g of 1-allyl-2,2,6,6-tetramethyl-4-hydroxypiperidine in 100 ml of xylene are heated under a gentle stream of nitrogen to about 140°. The methanol forming during the reaction is continuously distilled off, and after about 6 hours the reaction is virtually completed. The reaction mixture is diluted with 200 ml of toluene, extracted three times with 100 ml of water each time, dried over sodium sulphate and concentrated by evaporation. Crystallisation of the residue from hexane yields bis-(1-allyl-2,2,6,6-tetramethyl-4-piperidinyl) diethylmalonate (compound 18), m.p. 135°-136°.

Workup

  1. temperatureare heated under a gentle stream of nitrogen to about 140°
  2. distillationThe methanol forming during the reaction is continuously distilled off
  3. additionThe reaction mixture is diluted with 200 ml of toluene
  4. extractionextracted three times with 100 ml of water each time
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation
  7. customCrystallisation of the residue from hexane

Sources & evidence

ORD record
ord-9880888cada64eb0b2423ff6cef9425a
Source dataset
uspto-grants-1981_10
Patent number
US04293468

Reaction notes

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