Allyl bromide → 5-Allyl-1,2,5,6-tetrahydro-2,2,6,6-tetramethyl-4-piperidinopyridine
Reaction equation
[CH3:1][C:2]1([CH3:16])[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:5][C:4]([CH3:15])([CH3:14])[NH:3]1.[CH2:17](Br)[CH:18]=[CH2:19]>C(Cl)(Cl)Cl>[CH2:19]([CH:7]1[C:2]([CH3:16])([CH3:1])[NH:3][C:4]([CH3:15])([CH3:14])[CH:5]=[C:6]1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH:18]=[CH2:17]Participants
Procedure
2.2 of the 1,2,5,6-tetrahydro-2,2,6,6-tetramethyl-4-piperidinopyridine thus obtained and 1.2 g of allyl bromide were dissolved in 3 ml of chloroform and the solution was allowed to stand for 24 hours at room temperature. The crystals which precipitated were filtered off, washed with hexane and dissolved in 4 ml of concentrated aqueous ammonia; the solution was then extracted with hexane. The extract was dried over potassium carbonate and, after removing the hexane, 1.3 g of 5-allyl-1,2,5,6-tetrahydro-2,2,6,6-tetramethyl-4-piperidinopyridine were obtained. The compound showed a single spot on thin layer chromatography using a 0.25 mm thick layer of alumina (available from Merck & Co. under the trade name "60F 254") and using a mixture of benzene/hexane/ethyl acetate/triethylamine (2 : 2 1 : 0.5 by volume) s developing solvent; the Rf value was 0.80.
Workup
- customThe crystals which precipitated
- filtrationwere filtered off
- washwashed with hexane
- dissolutiondissolved in 4 ml of concentrated aqueous ammonia
- extractionthe solution was then extracted with hexane
- dry with materialThe extract was dried over potassium carbonate
- customafter removing the hexane
Sources & evidence
- ORD record
- ord-678ee08ed32249ca8d646b564bbcfbfb
- Source dataset
- uspto-grants-1978_02
- Patent number
- US04075165
Reaction notes
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