Water → HCID 22613817, compound

HRID 844551Notes

Reaction equation

HRID 844551 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:22][C:23](OCC)=[O:24])([C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[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>[CH3:21][C:16]1[CH:15]=[C:14]([C:11]2([CH2:22][CH2:23][OH:24])[CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:12]2)[CH:19]=[C:18]([CH3:20])[CH:17]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22613843HCID 22613843, compound

Product 1

HCID 22613817HCID 22613817, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-(1-benzyl-4-(3,5-dimethylphenyl)piperidin-4-yl)ethanoate (2.0 g) (see Preparation 9) was dissolved in anhydrous diethyl ether (50 ml), cooled in an ice-bath and lithium aluminium hydride (0.21 g) added portionwise. The mixture was stirred at room temperature for 45 minutes, water (0.3 ml) was carefully added, followed by 2N aqueous sodium hydroxide solution (0.3 ml) and further water (0.6 ml). The mixture was stirred for 20 minutes and the resulting granular precipitate removed by filtration and washed with diethyl ether. 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-(3,5-dimethylphenyl)-4-(2-hydroxyethyl)-N-benzylpiperidine (1.67 g) as an oil.

Workup

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

Sources & evidence

ORD record
ord-5fd71bc247624e2ba87d3f61d85fa085
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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