Hydrogen Peroxide → HCID 12788383, compound

A solution of 1.75 g of the free base 3-phenyl-4-piperidone of Example 50c, above, in 10 ml of dry THF is cooled to 5° C. and treated dropwise with 15 ml of lithium tri-secondarybutylborohydride in THF over a ten minute period under nitrogen. After the addition the mixture is stirred 18 hours at room temperature, then cooled to 0°-10° C. during dropwise addition of 10 ml of 10% aqueous NaOH solution. This is followed by addition of 7 ml of 30% aqueous hydrogen peroxide solution added at a rate sufficient to keep the pot temperature between 30°-40° C. The mixture is then stirred 18 hours at room temperature, followed by 1 hour of refluxing. The mixture is cooled and the phases are separated. The aqueous phase is extracted with chloroform. The combined organic phases are concentrated in vacuo to oil which is treated with 50 ml of cyclohexane and reconcentrated to an oil. This material is taken up in chloroform, and the solution is washed with saturated aqueous NaCl solution, and dried over anhydrous Na2SO4. Concentration in vacuo affords an oil which solidifies upon trituration with ether. A solid is then obtained, mp s 111°, 114°-117° C. Recrystallization from benzene affords cis-3-phenyl-4-piperidinol, mp s 115°, 117°-119° C.

1. additionAfter the addition the mixture
2. additionadded at a rate sufficient
3. custombetween 30°-40° C
4. stirringThe mixture is then stirred 18 hours at room temperature
5. waitfollowed by 1 hour
6. temperatureof refluxing
7. temperatureThe mixture is cooled
8. customthe phases are separated
9. extractionThe aqueous phase is extracted with chloroform
10. concentrationThe combined organic phases are concentrated in vacuo to oil which
11. additionis treated with 50 ml of cyclohexane
12. washthe solution is washed with saturated aqueous NaCl solution
13. dry with materialdried over anhydrous Na2SO4
14. concentrationConcentration in vacuo
15. customaffords an oil which
16. customA solid is then obtained
17. customs 111°, 114°-117° C
18. customRecrystallization from benzene

ORD record

ord-ccbbc96c5a53487fa76b007771c3e625

Source dataset

uspto-grants-1983_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04382141