6-[4-[4-[3-(4-Acetylpiperazin-1-yl)propoxy]phenyl]piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine → 4-Piperidin-4-ylphenol

HRID 2381097Notes

Reaction equation

HRID 2381097 reaction equation
C(N1CCN(CCC[O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:25][CH2:24][N:23](C4CCC5N(C(C(F)(F)F)=NN=5)N=4)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)CC1)(=O)C>[Pd].CO>[NH:23]1[CH2:24][CH2:25][CH:20]([C:17]2[CH:16]=[CH:15][C:14]([OH:13])=[CH:19][CH:18]=2)[CH2:21][CH2:22]1

Participants

4

Reactant 1

HCID 468935846-[4-[4-[3-(4-Acetylpiperazin-1-yl)propoxy]phenyl]piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 105115114-Piperidin-4-ylphenolYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 4-(4-hydroxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (obtained as described in Example 4.1, preparation of starting materials) (37.7 g, 121.86 mmol) and 5% palladium on carbon (7.6 g, 3.57 mmol) in methanol (380 mL) were stirred under an atmosphere of hydrogen at 5 bar and 25° C. for 2 hours. The catalyst was removed by filtration, washed with MeOH and the solvents evaporated. The crude material was triturated with diethyl ether, then the desired product collected by filtration and dried under vacuum to afford 4-(piperidin-4-yl)phenol (20.36 g, 94%) as a solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with MeOH
  3. customthe solvents evaporated
  4. customThe crude material was triturated with diethyl ether
  5. filtrationthe desired product collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-3061437bfa544ae4bd354d77c1dbc64e
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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