1-(2,2-Diphenylethyl)piperidin-4-one → 1-(2,2-Diphenylethyl)-4-methyl-4-piperidinol

HRID 1449062Notes

Reaction equation

HRID 1449062 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.[CH3:22][Mg]Br>O1CCCC1>[CH3:22][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

Participants

4

Reactant 2

HCID 125156351-(2,2-Diphenylethyl)piperidin-4-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 203750531-(2,2-Diphenylethyl)-4-methyl-4-piperidinol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.28 parts of 1-(2,2-diphenylethyl)-4-piperidinone in 5 parts by volume of tetrahydrofuran under nitrogen atmosphere is added 2 parts by volume of 3 M solution of methylmagnesium bromide. The resultant mixture is stirred for about 2.5 hours and then quenched with the careful addition of 5 parts by volume of 10% ammonium chloride. The mixture is left standing overnight, partitioned between water and ethyl acetate, and the organic layer separated. The organic layer is then dried with brine and magnesium sulfate, and concentrated to give 4-methyl-1-(2,2-diphenylethyl)-4-piperidinol, as yellow solid. This compound is represented by the following structural formula ##STR40##

Workup

  1. customquenched with the careful addition of 5 parts by volume of 10% ammonium chloride
  2. waitThe mixture is left
  3. custompartitioned between water and ethyl acetate
  4. customthe organic layer separated
  5. dry with materialThe organic layer is then dried with brine and magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-147ef1ad2cd4409f887076df6e895135
Source dataset
uspto-grants-1980_02
Patent number
US04188485

Reaction notes

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