Water → HCID 13607665, compound

HRID 652730Notes

Reaction equation

HRID 652730 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:25])[CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20](OCC)=[O:21])[CH2:16][CH2:15]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O>C(OCC)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:25])[CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([CH2:20][OH:21])[CH2:18][CH2:19]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 962WaterHCID 13607664HCID 13607664, compound

Product 1

HCID 13607665HCID 13607665, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

A solution of 41.4 g of N-[3-(4-tert.-butylphenyl)-2-methyl-propyl]-4-carbethoxy-piperidine in 100 ml of absolute diethyl ether is added dropwise to a suspension of 10 g of LiALH4 in 100 ml of absolute ether. An exothermic reaction ensues and the ether refluxes. When the reaction has subsided, the mixture is heated under reflux for 4 hours. 100 ml of water are then slowly added dropwise, with ice cooling. 500 ml of diethyl ether are added, the top layer is decanted and the smeary residue is triturated twice more with ether. The combined ether phases are washed with water, dried over Na2SO4 and concentrated. Distillation of the residue gives 21 g of N-[3-(4-tert.-butylphenyl)-2-methyl-propyl]-4-hydroxymethylpiperidine [B]. Boiling point 175°-178° C./0.2 mbar.

Workup

  1. customAn exothermic reaction ensues
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 4 hours
  4. customthe top layer is decanted
  5. customthe smeary residue is triturated twice more with ether
  6. washThe combined ether phases are washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. distillationDistillation of the residue

Sources & evidence

ORD record
ord-0158fc5f81cb47ca8836f5d583219ed0
Source dataset
uspto-grants-1987_06
Patent number
US04673683

Reaction notes

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