HCID 22126993, compound → HCID 22128196, compound

HRID 1858603Notes

Reaction equation

HRID 1858603 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=2)[CH:10]([OH:22])[CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]=O.C>[OH:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]2[OH:22])=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 22126993HCID 22126993, compound

Product 1

HCID 22128196HCID 22128196, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 57448735HCID 57448735, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.0 g (6.72 mmol) of (3RS,4RS)-1-benzyl-4-(4-hydroxymethyl-phenyl)-piperidin-3-ol in 100 ml of ethanol was hydrogenated at room temperature and 3 bar for 4 hours in the presence of 1.0 g of palladium oxide/charcoal (20%). For the working-up, the catalyst was filtered off under suction over Dicalit and the residue was washed twice with 50 ml of ethanol each time. The ethanol solution was evaporated under reduced pressure and the residue was chromatographed on silica gel using a 65:10:1 mixture of methylene chloride, methanol and ammonia as the eluent. There were obtained 1.1 g (79% of theory) of (3RS,4RS)-4-(4-hydroxymethyl-phenyl)-piperidin-3-ol as a colourless solid; MS: 207 (M)+.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationthe catalyst was filtered off under suction over Dicalit
  3. washthe residue was washed twice with 50 ml of ethanol each time
  4. customThe ethanol solution was evaporated under reduced pressure
  5. customthe residue was chromatographed on silica gel using
  6. additiona 65:10:1 mixture of methylene chloride, methanol and ammonia as the eluent

Sources & evidence

ORD record
ord-2e6a877e8b4547a9b71d8eb0b7990953
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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