Allyl bromide → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-(2-propenyl)piperidine

A mixture of 900 mg. (2.97 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]piperidine, 481 mg. (3.48 mmoles) of anhydrous potassium carbonate and 359 mg. (2.97 mmoles) of allyl bromide in 20 ml. of ethanol is heated at reflux for 23 hours. The reaction mixture is concentrated under reduced pressure and the residue dissolved in 250 ml. of saturated sodium bicarbonate and 200 ml. of dichloromethane. The organic extract is washed once with 100 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated under reduced pressure to an oil. The oil is purified via column chromatography on 125 g. of silica gel eluted with 25% cyclohexane-ether to yield 172 mg. (15%) of 3-[4-(1,1-dimethylheptyl)-2-allyloxyphenyl]-1-N-(2-propenyl)-piperidine as an oil and 411 mg. (40%) of the title compound as an oil.

1. additionA mixture of 900 mg
2. temperatureat reflux for 23 hours
3. concentrationThe reaction mixture is concentrated under reduced pressure
4. dissolutionthe residue dissolved in 250 ml
5. extractionThe organic extract
6. washis washed once with 100 ml
7. dry with materialof saturated sodium chloride, dried over magnesium sulfate
8. customevaporated under reduced pressure to an oil
9. customThe oil is purified via column chromatography on 125 g
10. washof silica gel eluted with 25% cyclohexane-ether
11. customto yield 172 mg

ORD record

ord-13fb1860210d41ebb32bb147f1a5a9d4

Source dataset

uspto-grants-1983_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04387229