Hydrochloric Acid → 1-[3-(p-Tert.amyl-phenyl)-2-methyl-propyl]-piperidine
Reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:16])[CH:14]=O)=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C1(C)C=CC=CC=1.Cl>C(O)=O.O>[C:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:16])[CH2:14][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 75 °C
Procedure
21.8 G. of 3-(p-tert.-amyl-phenyl)-2-methyl-propionaldehyde and 11.3 g. of piperidine are heated at reflux in 15 ml. of toluene in a water-separator under nitrogen gasification until the water-cleavage has been completed (6 hours). Subsequently, there are added dropwise at room temperature with stirring 6.9 g. of formic acid, the temperature rising to 36°-40° C. Then, the mixture is heated to 75° C. for 2 hours, 50 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 40 ml. of 6 N sodium hydroxide and the product is extracted with ether. The combined ether extracts are washed with water, dried over sodium sulfate and evaporated. By distillation, there is obtained pure 1-[3-(p-tert.-amyl-phenyl)-2-methyl-propyl]-piperidine having a boiling point of 160° C./0.15 Torr.
Workup
- temperatureat reflux in 15 ml
- custom(6 hours)
- additionSubsequently, there are added dropwise at room temperature
- customrising to 36°-40° C
- customThe toluene solution is separated
- extractionof 6 N sodium hydroxide and the product is extracted with ether
- washThe combined ether extracts are washed with water
- dry with materialdried over sodium sulfate
- customevaporated
- distillationBy distillation
Sources & evidence
- ORD record
- ord-229c649257aa426583143dce434d7e7f
- Source dataset
- uspto-grants-1980_05
- Patent number
- US04202894
Reaction notes
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