HCID 22127314, compound → HCID 22128636, compound

HRID 1858553Notes

Reaction equation

HRID 1858553 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:10]([OH:21])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[C:17]1([CH3:20])[CH:16]=[CH:15][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]2[OH:21])=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 22127314HCID 22127314, compound

Product 1

HCID 22128636HCID 22128636, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2.5 g (8.9 mmol) of (3RS,4RS)-1-benzyl-4-(p-tolyl)-piperidin-3-ol in 100 ml of methanol was hydrogenated at 5 bar at room temperature for 18 hours using a palladium (10%)-carbon catalyst. For the working up, the catalyst was filtered off, washed with methanol and the solution obtained was evaporated under reduced pressure. For purification, the residue was chromatographed on silica gel using a 5:1:0.1 mixture of methylene chloride, methanol and ammonia as the eluent. There were obtained 1.15 g (68% of theory) of (3RS,4RS)-4-(p-tolyl)-piperidin-3-ol as a colourless solid; MS: 191 (M)+.

Workup

  1. filtrationFor the working up, the catalyst was filtered off
  2. washwashed with methanol
  3. customthe solution obtained
  4. customwas evaporated under reduced pressure
  5. customFor purification
  6. customthe residue was chromatographed on silica gel using
  7. additiona 5:1:0.1 mixture of methylene chloride, methanol and ammonia as the eluent

Sources & evidence

ORD record
ord-3ae457b5d1f540b9826ed720dda50401
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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