Dimethyl Sulfoxide → N-(2,2,6,6-tetramethyl-4-piperidylidene)-2-methyl-1-amino-1-propene

HRID 2164690Notes

Reaction equation

[CH3:1][C:2]1([CH3:15])[CH2:7][C:6](=[N:8][CH2:9][C:10]([CH3:12])=[CH2:11])[CH2:5][C:4]([CH3:14])([CH3:13])[NH:3]1.CC([O-])(C)C.[K+].CS(C)=O>C1(C)C=CC=CC=1>[CH3:13][C:4]1([CH3:14])[CH2:5][C:6](=[N:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:7][C:2]([CH3:15])([CH3:1])[NH:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

162.5 g of the N-(2,2,6,6-tetramethyl-4-piperidylidene)-2-methylallylamine are dissolved in 162 ml of toluene in a 500 ml three-necked flask with reflux condenser, and 4.86 g of potassium tert-butylate are added. To the reaction mixture are then added, with stirring, 50 ml of dimethyl sulfoxide, and stirring is maintained at 50° C. for 8 hours. The organic phase is afterwards extracted with 100 ml of distilled water, and the organic part, after separation of the solvent, is distilled to yield 136.9 g of N-(2,2,6,6-tetramethyl-4-piperidylidene)-2-methyl-1-amino-1-propene as a colourless liquid, b.p. 56° C. at 40 Pa (82% of theory).

Workup

temperaturewith reflux condenser
additionTo the reaction mixture are then added
extractionThe organic phase is afterwards extracted with 100 ml of distilled water
customthe organic part, after separation of the solvent
distillationis distilled

Sources & evidence

ORD record: ord-533194612e1b46cba63b873a91254b78
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04506099

Reaction notes

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