1-Benzyl-4-piperidone → 1,4-dibenzylpiperidin-4-ol

HRID 1901084Notes

Reaction equation

HRID 1901084 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([N:17]1[CH2:22][CH2:21][C:20]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([OH:23])[CH2:19][CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 178418336HCID 178418336, compound

Product 1

HCID 47141251,4-dibenzylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of benzyl magnesium chloride (40 ml of 2.0 M soln. in THF, 80 mmol)in THF (80 ml) was added 1-benzyl-4-piperidinone (7.4 ml, 40 mmol) over 7 min. and stirred overnight. The o reaction mixture was poured over ice and extracted with ether (2×). The combined ether extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo to a pale green syrup. This material was chromatographed on silica with 50-60% EtOAc/hexane as eluent. The appropriate fractions were combined and concentrated in vacuo to afford the product as an off white solid.

Workup

  1. customThe o reaction mixture
  2. additionwas poured over ice
  3. extractionextracted with ether (2×)
  4. washThe combined ether extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo to a pale green syrup
  7. customThis material was chromatographed on silica with 50-60% EtOAc/hexane as eluent
  8. concentrationconcentrated in vacuo
  9. customto afford the product as an off white solid

Sources & evidence

ORD record
ord-b59f2f2e00c0473cb6fc8af15bad02e3
Source dataset
uspto-grants-1996_11
Patent number
US05576313

Reaction notes

Loading…