Ammonia → 2,2,6,6-Tetramethyl-3-(prop-2-en-1-yl)piperidin-4-one
Reaction equation
[CH2:1]([CH:4]1[C:9]([CH3:11])([CH3:10])[NH:8][C:7]([CH3:13])([CH3:12])[CH:6]=[C:5]1N1CCCCC1)[CH:2]=[CH2:3].C([O-])(=[O:22])C.[Na+].C(=O)(O)[O-].[Na+].N>C(O)(=O)C.O>[CH2:1]([CH:4]1[C:5](=[O:22])[CH2:6][C:7]([CH3:13])([CH3:12])[NH:8][C:9]1([CH3:11])[CH3:10])[CH:2]=[CH2:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
1.46 g of the 5-allyl-1,2,5,6-tetrahydro-2,2,6,6-tetramethyl-4-piperidinopyridine thus obtained were dissolved in a mixture of 3 ml of acetic acid, 1.5 g of sodium acetate and 3 ml of water, and the solution was allowed to stand overnight. To the solution were then added 6.0 g of sodium bicarbonate and 3 ml of concentrated aqueous ammonia; the solution was then extracted with hexane. The hexane extract was dried over magnesium sulphate and then treated with charcoal giving, after removal of the hexane, 0.91 g of 3-allyl-2,2,6,6-tetramethyl-4-piperidone. On thin layer chromatography using a 0.25 mm thick layer of alumina and a mixture of benzene, hexane, ethyl acetate and triethylamine (2 : 2 : 1 : 0.5 by volume) as developing solvent, the compound showed a single spot having an Rf value of 0.70.
Workup
- extractionthe solution was then extracted with hexane
- extractionThe hexane extract
- dry with materialwas dried over magnesium sulphate
- additiontreated with charcoal giving
- customafter removal of the hexane, 0.91 g of 3-allyl-2,2,6,6-tetramethyl-4-piperidone
- additiona mixture of benzene, hexane, ethyl acetate and triethylamine (2 : 2 : 1 : 0.5 by volume)
Sources & evidence
- ORD record
- ord-dcb4d7d6b64346b3abef2d6038d717d5
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04097587
Reaction notes
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