Water → HCID 22613827, compound

HRID 844548Notes

Reaction equation

HRID 844548 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:24][C:25](OCC)=[O:26])([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C.ClCCl>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[C:11]1([CH2:24][CH2:25][OH:26])[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22613816HCID 22613816, compound

Product 1

HCID 22613827HCID 22613827, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-(1-benzyl-4-(2-naphthyl)piperidin-4-yl)ethanoate (5.8 g) (see Preparation 4) was dissolved in anhydrous diethyl ether (100 ml), cooled in an ice-bath and lithium aluminium hydride (0.57 g) added, portionwise. The mixture was stirred at room temperature for 30 minutes, water (0.8 ml) was then carefully added followed by 2N aqueous sodium hydroxide solution (0.8 ml) and further water (1.6 ml). The mixture was stirred for 20 minutes and the resulting granular precipitate removed by filtration. The solvent was removed from the filtrate under reduced pressure to give a solid which was dissolved in dichloromethane, dried over anhydrous sodium sulphate and the solvent again removed under reduced pressure to yield 4-(2-naphthyl)-4-(2-hydroxyethyl)-N-benzylpiperidine (2.2 g) as a white solid.

Workup

  1. temperaturecooled in an ice-bath
  2. stirringThe mixture was stirred for 20 minutes
  3. customthe resulting granular precipitate removed by filtration
  4. customThe solvent was removed from the filtrate under reduced pressure
  5. customto give a solid which
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solvent again removed under reduced pressure

Sources & evidence

ORD record
ord-124bae5a4e9544859f59e4807f994338
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

Loading…