1-benzyl-2,2-dimethylpiperidin-4-one → 1-Benzyl-2,2-dimethylpiperidin-4-ol

HRID 1821981Notes

Reaction equation

HRID 1821981 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C:9]1([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][C:9]1([CH3:16])[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 40709121-benzyl-2,2-dimethylpiperidin-4-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 140285381-Benzyl-2,2-dimethylpiperidin-4-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 1-benzyl-2,2-dimethyl-piperidin-4-one (1.0 g, 4.6 mmol) and tetrahydrofuran (20 mL) and cool to 0° C. Add lithium aluminum hydride (0.175 g, 4.6 mmol) with stirring. After 30 min., warm to ambient temperature. After 30 min., quench the reaction mixture with water (50 mL). Extract with ethyl acetate (2×75 mL), combine the organic layers and wash with aqueous NaCl solution (50 mL), dry over sodium sulfate, filter and concentrate to obtain the title compound (1.0 g, 100%). Mass spectrum (electrospray): m/z=220.1 (M+1); 1H NMR (CDCl3): 7.3 (m, 5H), 4.0 (m, 1H), 3.8 (m, 1H), 3.0 (m, 1H), 2.6 (m, 1H), 2.3 (m, 1H), 1.8 (m, 2H), 1.4 (m, 3H), 1.25 (s, 3), 1.1 (s, 3H).

Workup

  1. waitAfter 30 min.
  2. customquench the reaction mixture with water (50 mL)
  3. extractionExtract with ethyl acetate (2×75 mL)
  4. washwash with aqueous NaCl solution (50 mL)
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-3c6b90fb386747cda83e76a6d5306834
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

Loading…