Benzene → HCID 12515636, compound

HRID 1449059Notes

Reaction equation

HRID 1449059 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][N:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC=CC=1.[C:28]([Li])([CH3:31])([CH3:30])[CH3:29]>CCCCC>[C:28]([C:12]1([OH:15])[CH2:13][CH2:14][N:9]([CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:11]1)([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 241BenzeneHCID 125156351-(2,2-Diphenylethyl)piperidin-4-oneHCID 178418306HCID 178418306, compound

Product 1

HCID 12515636HCID 12515636, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a stirred solution of 2 parts of 1-(2,2-diphenylethyl)-4-piperidinone in 50 parts by volume of benzene under nitrogen atmosphere is added 30 parts of 1.6 M solution of tertiary-butyllithium in pentane. The resultant solution is stirred for about 24 hours and then quenched with the careful addition of 60 parts by volume of 10% ammonium chloride solution. After 1 hour, the organic layer is separated, washed with water and brine, dried with magnesium sulfate, and concentrated to give clear red oil. This oil is chromatographed on silica gel using successively methylene chloride and 10% ethanol-methylene chloride solution as eluents to give pale yellow solid which upon sublimation affords 4-tert-butyl-1-(2,2-diphenylethyl)-4-piperidinol. This compound melts at about 105°-110° C. and is represented by the following structural formula ##STR36##

Workup

  1. customquenched with the careful addition of 60 parts by volume of 10% ammonium chloride solution
  2. customthe organic layer is separated
  3. washwashed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customto give clear red oil
  7. customThis oil is chromatographed on silica gel using successively methylene chloride and 10% ethanol-methylene chloride solution as eluents
  8. customto give pale yellow solid which upon sublimation

Sources & evidence

ORD record
ord-1b56fa36966844a4acc5f2aa89331289
Source dataset
uspto-grants-1980_02
Patent number
US04188485

Reaction notes

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