Acetic Acid → 1-(4-Cyclohexylpiperidin-4-yl)butan-1-one
Reaction equation
C(O)(=O)C.Cl.[C:6]([C:11]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)(=[O:10])[CH2:7][CH2:8][CH3:9]>O1CCOCC1.[Rh]>[CH:17]1([C:11]2([C:6](=[O:10])[CH2:7][CH2:8][CH3:9])[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
In a Parr bomb under a hydrogen pressure of 6 bar, 100 mg of rhodium on alumina and 0.2 mL of acetic acid are added to a solution of 100 mg (0.5 mmol) of 4-butyryl-4-phenylpiperidine hydrochloride in 10 mL of dioxane. The reaction medium is heated at 80° C. for 12 hours. The reaction is stopped and then filtered through Celite and washed with dichloromethane. The solvents are evaporated off and the residue is taken up in water, basified with 1N sodium hydroxide solution and extracted with ethyl acetate. The organic phases are dried over sodium sulfate. The solvents are evaporated off and the residue is chromatographed on silica gel (eluent: 9/1 dichloromethane/methanol). 51.2 mg of 1-(4-cyclohexylpiperidin-4-yl)-butan-1-one in the form of a white powder are obtained in a yield of 61%.
Workup
- filtrationfiltered through Celite
- washwashed with dichloromethane
- customThe solvents are evaporated off
- extractionextracted with ethyl acetate
- dry with materialThe organic phases are dried over sodium sulfate
- customThe solvents are evaporated off
- customthe residue is chromatographed on silica gel (eluent: 9/1 dichloromethane/methanol)
Sources & evidence
- ORD record
- ord-bfe8099039c44b818dcca6bef6556c83
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877968B2
Reaction notes
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