1-Benzyl-3-(3,4-dimethoxyphenyl)piperidin-3-ol → HCID 13066745, compound

HRID 851131Notes

Reaction equation

HRID 851131 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)([OH:14])[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([C:10]2([OH:14])[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 130667441-Benzyl-3-(3,4-dimethoxyphenyl)piperidin-3-olHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13066745HCID 13066745, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5 g of 10% palladized carbon and a solution of 9.8 g of N-benzyl-3-(3,4-dimethoxyphenyl)-3-hydroxy-piperidine [described in French patent No. 2,310,761] in 100 ml of ethanol was placed in an autoclave and hydrogen was introduced to obtain a pressure of 50 kg/cm2. The autoclave was sealed and was heated at 100° C. and the hydrogen pressure stabilized at 65 kg/cm2. The mixture was stirred at 100° C. for 32 hours and was then cooled and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 75-20-5 chloroform-methanol-triethylamine mixture yielded 5.3 g of 3-(3,4-dimethoxyphenyl)-3-hydroxy-piperidine.

Workup

  1. additionA mixture of 5 g of 10%
  2. additionwas introduced
  3. customto obtain a pressure of 50 kg/cm2
  4. customThe autoclave was sealed
  5. temperaturewas then cooled
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness under reduced pressure
  8. customthe residue was chromatographed over silica gel
  9. washElution with a 75-20-5 chloroform-methanol-triethylamine mixture

Sources & evidence

ORD record
ord-880b19d1a9c043e9b3422722945db92d
Source dataset
uspto-grants-1983_05
Patent number
US04382942

Reaction notes

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