Hydrochloric Acid → 6-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxylic acid

HRID 1714864Notes

Reaction equation

HRID 1714864 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[N:16][C:15]([C:18]([O:20]C)=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.O.[OH-].[Li+].Cl>C1COCC1.O>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[N:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68505610Methyl 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxylate

Product 1

HCID 462254266-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxylate (800 mg, 2.1 mmol) and lithium hydroxide monohydrate (352 mg, 8.4 mmol) in THF (10 mL) and water (5 mL) was stirred at r.t. overnight, then acidified with 1M aqueous HCl (9 mL). Volatile materials were removed in vacuo. The residue was diluted with water and extracted with EtOAc. The organic extract was washed with diluted brine, dried (Na2SO4), concentrated and swished with Et2O to give the title compound as a white powder. 1H NMR (400 MHz, acetone-d6): δ 1.97 (m, 2H), 2.15-2.21 (m, 2H), 4.00-4.10 (m, 4H), 5.04-5.08 (m, 1H), 7.13 (t, 1H), 7.39 (m, 2H), 7.63-7.69 (m, 2H), 7.94 (d, 1H).

Workup

  1. customVolatile materials were removed in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with diluted brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a0181077ca404f4f8125e1c489677742
Source dataset
uspto-grants-2010_09
Patent number
US07799787B2

Reaction notes

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