Hydrochloric Acid → 5-(3,4-Dimethoxyphenyl)-2-{1-[(3-hydroxyphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 524209Notes

Reaction equation

HRID 524209 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23](=[O:24])[C:22]([CH3:26])([CH3:25])[C:21]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=4)=[N:20]3)[CH2:15][CH2:14]2)=[O:12])[CH:6]=1)(=O)C.[OH-].[Na+].Cl>C1COCC1.CC(C)=O.CO>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([C:21]2[C:22]([CH3:26])([CH3:25])[C:23](=[O:24])[N:19]([CH:16]3[CH2:17][CH2:18][N:13]([C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([OH:4])[CH:6]=4)=[O:12])[CH2:14][CH2:15]3)[N:20]=2)[CH:32]=[CH:31][C:30]=1[O:33][CH3:34]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 462027213-({4-[3-(3,4-Dimethoxyphenyl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}carbonyl)phenyl acetate

Product 1

HCID 462066295-(3,4-Dimethoxyphenyl)-2-{1-[(3-hydroxyphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 g 3-({4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}carbonyl)phenyl acetate (compound described in example 12) are dissolved in a mixture of 200 ml THF, 100 ml acetone and 200 ml of methanol. To this mixture 200 ml of 2 M methanolic sodium hydroxide solution are added, and the reaction mixture is stirred at RT for 1 h until the reaction is completed according to TLC analysis. The reaction mixture is acidified with concentrated aqueous hydrochloric acid, and the solvents are largely removed under reduced pressure, while the crude product is precipitating. The solids are collected and washed with water to yield the title compound.

Workup

  1. customthe solvents are largely removed under reduced pressure, while the crude product
  2. customis precipitating
  3. customThe solids are collected
  4. washwashed with water

Sources & evidence

ORD record
ord-1eaee3bae7134365b36d7ee863b163ce
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

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