Sodium Hydroxide → HCID 22628343, compound

HRID 1764467Notes

Reaction equation

HRID 1764467 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([C:12]1([OH:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1C=CC=CC=1.CCOCC.Cl.CC(C)=O.C(N(CC)CC)C>[ClH:3].[CH2:5]([C:12]1([OH:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

10

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 981524-Benzyl-4-piperidinolHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 22628343HCID 22628343, compound

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 241BenzeneSolventHCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2 parts of (p-chlorophenyl)diphenyl carbinol and 8 parts of malonic acid are heated at 170° for 31 hours. This mixture is cooled and then dissolved in hot ethanol, affording 3-p-chlorophenyl-3,3-diphenylpropionic acid. 1 Part of 3-(p-chlorophenyl)3,3-triphenylpropionic acid is then refluxed with 5 parts of thionyl chloride for 4 hours and the excess thionyl chloride is removed in vacuum to provide the crude 3-(p-chlorophenyl)3,3-diphenylpropionyl chloride. 9 Parts of this 3-(p-chlorophenyl)-3,3-triphenylpropionyl chloride are then reacted with 27.0 parts of 4-benzyl-4-hydroxypiperidine in the presence of 4 parts of triethylamine in benzene. The resulting amide is reduced with 5 parts of lithium aluminum hydride in ether at reflux for 2.5 hours. The reaction mixture is cooled and treated with 15% aqueous sodium hydroxide solution to decompose any unreacted lithium aluminum hydride. The reaction mixture is then filtered and washed with ether. The ether solution is evaporated to give an oil. This oil is then slurried in 10% HCl and extracted with ether. The aqueous phase which contains an insoluble oil is extracted with methylene chloride, and the methylene chloride extract dried over anhydrous sodium sulfate. Evaporation of this methylene chloride solution gives a solid which is taken up in acetone and precipitated with ether which affords 1-[3-p-chlorophenyl)-3,3-diphenylpropyl]-4-benzyl-4-hydroxypiperidine hydrochloride having the following structural formula ##STR20##

Workup

  1. customthe excess thionyl chloride is removed in vacuum
  2. customto provide the crude 3-(p-chlorophenyl)3,3-diphenylpropionyl chloride
  3. temperatureat reflux for 2.5 hours
  4. temperatureThe reaction mixture is cooled
  5. filtrationThe reaction mixture is then filtered
  6. washwashed with ether
  7. customThe ether solution is evaporated
  8. customto give an oil
  9. extractionextracted with ether
  10. extractionis extracted with methylene chloride
  11. extractionthe methylene chloride extract
  12. dry with materialdried over anhydrous sodium sulfate
  13. customEvaporation of this methylene chloride solution
  14. customgives a solid which
  15. customprecipitated with ether which

Sources & evidence

ORD record
ord-470886afb75843a485224d34f80a82bb
Source dataset
uspto-grants-1978_09
Patent number
US04116963

Reaction notes

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