Hydrochloric Acid → 2,6-Diethyl-2,3,6-trimethylpiperidin-4-one
Reaction equation
[CH2:1]([C:3]1([CH3:14])N=[C:7]([CH2:9][CH3:10])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2].Cl.C(=O)([O-])[O-:17].[K+].[K+]>[Br-].[NH4+].CO>[CH2:1]([C:3]1([CH3:14])[CH:9]([CH3:10])[C:7](=[O:17])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2]Participants
Conditions
- Temperature
- 10 °C
Procedure
19.6 g of 2,4,6-triethyl-2,6-dimethyl-1,2,5,6-tetrahydropyrimidine and 0.4 g of ammonium bromide were added to 200 ml of methanol. Whilst maintaining the mixture at 10° C and stirring, 10 g of 37% hydrochloric acid were added dropwise. After completion of the addition, the resulting mixture was stirred at room temperature for 4 hours and there were then added dropwise 20 ml of 18% hydrochloric acid. The mixture was then heated at 30°-40° C for 7 hours and allowed to stand overnight at room temperature. After this, the mixture was made alkaline by the addition of a 40% aqueous solution of potassium carbonate, the methanol was evaporated off under reduced pressure, and the mixture was extracted with diethyl ether. The ethereal solution was dried over potassium carbonate and the diethyl ether was then removed. The residue was distilled under reduced pressure, giving 15.1 g of 2,6-diethyl-2,3,6-trimethyl-4-piperidone as an oil boiling at 91° - 93° C/2.0 mmHg.
Workup
- additionAfter completion of the addition
- stirringthe resulting mixture was stirred at room temperature for 4 hours
- temperatureThe mixture was then heated at 30°-40° C for 7 hours
- customthe methanol was evaporated off under reduced pressure
- extractionthe mixture was extracted with diethyl ether
- dry with materialThe ethereal solution was dried over potassium carbonate
- customthe diethyl ether was then removed
- distillationThe residue was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-965b55c329bd4014bd62c4dd0a354698
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04097587
Reaction notes
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