Hydrochloric Acid → HCID 66990563, compound

HRID 454691Notes

Reaction equation

HRID 454691 reaction equation
[OH-].[Na+].CC(O)C.[C:7]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([OH:44])=[C:23]([CH:43]=2)[C:24]([NH:26][C:27]2[CH:36]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:34]=[CH:33][C:28]=2[C:29]([O:31]C)=[O:30])=[O:25])[CH2:12][CH2:11]1)(=[O:9])[CH3:8].[ClH:45]>O>[ClH:45].[C:7]([N:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([OH:44])=[C:23]([CH:43]=2)[C:24]([NH:26][C:27]2[CH:36]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:34]=[CH:33][C:28]=2[C:29]([OH:31])=[O:30])=[O:25])[CH2:14][CH2:15]1)(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 58508769HCID 58508769, compound

Product 1

HCID 66990563HCID 66990563, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 2.0 mol/L aqueous solution of sodium hydroxide (0.24 mL) was added to a 2-propanol (1.5 mL) suspension of the obtained methyl 2-(5-(2-(4-acetylpiperazin-1-yl)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoate (0.083 g), followed by stirring at 50° C. for 1 hour. The reaction mixture was cooled to room temperature, and water was added thereto. After adjusting the pH to 6.5 with 1.0 mol/L hydrochloric acid, the solvent was evaporated under reduced pressure. Water was added to the obtained residue, and the solid substance was collected by filtration. Ethyl acetate (2.0 mL) and a 4.0 mol/L hydrogen chloride-dioxane solution (0.10 mL) were added to the obtained solid substance, followed by stirring at room temperature for 3 hours and 30 minutes. The solid substance was collected from the reaction mixture by filtration to obtain 0.038 g of 2-(5-(2-(4-acetylpiperazin-1-yl)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoic acid hydrochloride as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. additionWater was added to the obtained residue
  4. filtrationthe solid substance was collected by filtration
  5. additionEthyl acetate (2.0 mL) and a 4.0 mol/L hydrogen chloride-dioxane solution (0.10 mL) were added to the obtained solid substance
  6. stirringby stirring at room temperature for 3 hours and 30 minutes
  7. filtrationThe solid substance was collected from the reaction mixture by filtration

Sources & evidence

ORD record
ord-ede0e332ed2249f0a719e5e64778f9e8
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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