HCID 19097379, compound → HCID 19097382, compound

HRID 486048Notes

Reaction equation

HRID 486048 reaction equation
[CH3:1][CH:2]1[C:7]([CH3:12])([CH2:8][CH2:9][CH2:10][OH:11])[CH:6]([CH3:13])[CH2:5][CH2:4][N:3]1CC1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH3:1][CH:2]1[C:7]([CH3:12])([CH2:8][CH2:9][CH2:10][OH:11])[CH:6]([CH3:13])[CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 2

HCID 19097379HCID 19097379, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19097382HCID 19097382, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,3,4-trimethyl-l-(phenylmethyl)-3-piperidinepropanol (45.0 g, 163 mmol), ethanol (200 mL) and 10% palladium on carbon (4.5 g) was placed on a Parr hydrogenator at 50 psi of hydrogen pressure until hydrogen uptake ceased. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was crystallized from ether to afford 24.9 g (82%) of 2.3.4-trimethyl-3-piperidinepropanol. The product was recrystallized from ethyl acetate and had a melting point of 89-91° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-e3013e3eb62f49e4a6700992c3f2990a
Source dataset
uspto-grants-1994_03
Patent number
US05290789

Reaction notes

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