Hydrochloric Acid → 1-[3-(4-tert-Butylphenyl)-2-methylpropyl]-3,5-dimethylpiperidine
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:15])[CH:13]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][CH:17]1[CH2:22][CH:21]([CH3:23])[CH2:20][NH:19][CH2:18]1.O.Cl>C1(C)C=CC=CC=1.C(O)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:15])[CH2:13][N:19]2[CH2:20][CH:21]([CH3:23])[CH2:22][CH:17]([CH3:16])[CH2:18]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 80 °C
Procedure
67.8 g of 3-(p-tert.butyl-phenyl)-2-methyl-propionaldehyde and 50 g of 3,5-dimethyl-piperidine are heated at reflux in 50 ml of toluene in a water-separator under nitrogen gasification until the water-cleavage has been completed (16 hours). Subsequently, there are added dropwise at room temperature while stirring 16.8 g of formic acid, the temperature rising to 36°-40° C. The mixture is then heated to 80° C. for 1 hour. 165 ml of 2-N hydrochloric acid are added to the cooled solution, the toluene solution is separated, the aqueous-hydrochloric acid solution is made alkaline with 66 ml of 6-N sodium hydroxide and the product is extracted with ether. The combined ether extracts are washed with water, dried over sodium sulphate and evaporated. By distillation there is obtained pure 1-[3-(p-tert.butyl-phenyl)-2-methyl-propyl]-3,5-dimethyl-piperidine of boiling point 113°-114° C./0.09 Torr.
Workup
- custom(16 hours)
- additionSubsequently, there are added dropwise at room temperature
- customrising to 36°-40° C
- customthe toluene solution is separated
- extractionthe product is extracted with ether
- washThe combined ether extracts are washed with water
- dry with materialdried over sodium sulphate
- customevaporated
- distillationBy distillation there
Sources & evidence
- ORD record
- ord-381fd634d7644d6bb09bb3ecafa09f83
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04241058
Reaction notes
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