1-Benzyl-4-piperidone → HCID 57979767, compound

HRID 1868087Notes

Reaction equation

HRID 1868087 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[CH2:14]([N:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH4+].[Cl-]>C1COCC1>[CH2:14]([N:21]1[CH2:26][CH2:25][C:24]([OH:27])([C:2]2[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:23][CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 2208322-Bromo-3-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 57979767HCID 57979767, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following the procedure of N. I. Carruthers et al. (J. Med. Chem. 2005, 48, 1857-1872), to a −78° C. solution of 2-bromo-3-methylpyridine (10.0 g, 7.1 mL, 57.1 mmol) in THF (150 mL) was added drop wise a solution of n-BuLi (2.5 M in hexanes, 25.1 mL, 62.8 mmol) over 10 min. After 1.5 h a solution of N-benzyl-4-piperidone (10.8 g, 57.1 mmol) in THF (20 mL) was added drop wise over 15 min and the mixture was allowed to slowly warm to room temperature overnight. After 18 h sat. NH4Cl solution (40 mL) was added and the mixture was concentrated. The resulting residue was diluted with 1N NaHCO3 (100 ml) and extracted with EtOAc. The combined organic phase washed with brine, dried (MgSO4), and concentrated. Flash chromatography afforded the alcohol (8.1 g), an orange viscous oil, in 50% yield.

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe resulting residue was diluted with 1N NaHCO3 (100 ml)
  3. extractionextracted with EtOAc
  4. washThe combined organic phase washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-74d43ee6d2794b429ce6ae66bc566512
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

Loading…