Hydrochloric Acid → HCID 68433890, compound

HRID 1867367Notes

Reaction equation

HRID 1867367 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][OH:16])[CH2:9]1)C1C=CC=CC=1.[ClH:17].O1CCOCC1>CO.[OH-].[OH-].[Pd+2]>[ClH:17].[OH:16][CH2:15][CH:10]1[CH:11]([OH:14])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 36827051-benzyl-3-(hydroxymethyl)piperidin-4-ol

Product 1

HCID 68433890HCID 68433890, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 1 g (4.52 mmol) (rac)-1-benzyl-3-hydroxymethyl-piperidin-4-ol (ca 1:1 diast mixture, Synthesis (1999), 11, 1937-1943) in 25 ml of MeOH was treated with a solution of HCl in dioxane (1.24 ml, 4 M in dioxane, 4.97 mmol) and 95 mg of Pd(OH)2/C (20%) and was stirred over H2-atmosphere for 16 h. After filtration, new catalyst was added (95 mg of Pd(OH)2/C (20%)) and stirred over H2-atmosphere for 2 days. After filtration, the solution was evaporated under reduced pressure to yield 0.66 g (86%) of the title compound as a ca 1:1 cis/trans mixture, MS: 132.3 (MH+).

Workup

  1. filtrationAfter filtration, new catalyst
  2. additionwas added (95 mg of Pd(OH)2/C (20%))
  3. stirringstirred over H2-atmosphere for 2 days
  4. filtrationAfter filtration
  5. customthe solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fd2ae68716854321a1019fb21c656525
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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