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

HRID 2164690
Notes
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Reaction equation

HRID 2164690 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 20405357N-(2,2,6,6-tetramethyl-4-piperidylidene)-2-methylallylamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 20405359N-(2,2,6,6-tetramethyl-4-piperidylidene)-2-methyl-1-amino-1-propeneYield 84.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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

  1. temperaturewith reflux condenser
  2. additionTo the reaction mixture are then added
  3. extractionThe organic phase is afterwards extracted with 100 ml of distilled water
  4. customthe organic part, after separation of the solvent
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes