HCID 15512819, compound → HCID 18679667, compound

HRID 2268076Notes

Reaction equation

HRID 2268076 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])([OH:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO>[F:21][C:19]1[CH:18]=[CH:17][C:16]([O:22][CH3:23])=[C:15]([C:11]2([OH:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:20]=1

Participants

3

Reactant 1

HCID 15512819HCID 15512819, compound

Product 1

HCID 18679667HCID 18679667, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a round bottom flask at room temperature was placed with 1.95 g (6.18 mmole) 1-benzyl-4-(5-fluoro-2-methoxy-phenyl)-4-hydroxypiperidine, dry MeOH (40 mL), and the system purged with N2 for 5 min. To the solution, 1.95 g of 10% palladium on carbon was added. The system was again purged with N2 for 5 minutes followed by addition of 2 mL formic acid (88%). The resulting mixture was stirred at room temperature under N2 for one day. At this point, a further 2 mL of formic acid (88%) was added. The reaction was continued for 2.5 days. The mixture was filtered through celite, and concentrated to afford of 4-(5-fluoro-2-methoxy-phenyl)-4-hydroxypiperidine (0.95 g, 69% yield) as a yellow oil.

Workup

  1. customthe system purged with N2 for 5 min
  2. additionTo the solution, 1.95 g of 10% palladium on carbon was added
  3. customThe system was again purged with N2 for 5 minutes
  4. additionfollowed by addition of 2 mL formic acid (88%)
  5. additionAt this point, a further 2 mL of formic acid (88%) was added
  6. waitThe reaction was continued for 2.5 days
  7. filtrationThe mixture was filtered through celite
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-77ddc4d114964ae7895bc409eafd66ba
Source dataset
uspto-grants-2001_12
Patent number
US06326381B1

Reaction notes

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