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Hydrochloric Acid → 2-(2-Hydroxy-5-(1-isopropylpiperidin-4-yl)benzamido)-4-phenylbenzoic acid

HRID 454724
Notes
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Reaction equation

HRID 454724 reaction equation
[OH-].[Na+].CC(O)C.[OH:7][C:8]1[CH:32]=[CH:31][C:30]([CH:33]2[CH2:38][CH2:37][N:36]([CH:39]([CH3:41])[CH3:40])[CH2:35][CH2:34]2)=[CH:29][C:9]=1[C:10]([NH:12][C:13]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=[CH:19][C:14]=1[C:15]([O:17]C)=[O:16])=[O:11].Cl>O>[OH:7][C:8]1[CH:32]=[CH:31][C:30]([CH:33]2[CH2:34][CH2:35][N:36]([CH:39]([CH3:41])[CH3:40])[CH2:37][CH2:38]2)=[CH:29][C:9]=1[C:10]([NH:12][C:13]1[CH:22]=[C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:20]=[CH:19][C:14]=1[C:15]([OH:17])=[O:16])=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14798Sodium Hydroxide2×HCID 58508803Methyl 2-(2-hydroxy-5-(1-isopropylpiperidin-4-yl)benzamido)-4-phenylbenzoate

Product 1

HCID 585086142-(2-Hydroxy-5-(1-isopropylpiperidin-4-yl)benzamido)-4-phenylbenzoic acidYield 74.3%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 2.0 mol/L aqueous solution of sodium hydroxide (0.27 mL) was added to a 2-propanol (1.5 mL) suspension of the obtained methyl 2-(2-hydroxy-5-(1-isopropylpiperidin-4-yl)benzamido)-4-phenylbenzoate (0.086 g), followed by stirring at 50° C. for 1 hour. A 2.0 mol/L aqueous solution of sodium hydroxide (0.091 mL) was added to the reaction mixture, followed by stirring at 50° C. for 30 minutes. The reaction mixture was cooled to room temperature, and water was added thereto. After adjusting the pH to 6.0 with 1.0 mol/L hydrochloric acid, the solid substance was collected by filtration to obtain 0.062 g of 2-(2-hydroxy-5-(1-isopropylpiperidin-4-yl)benzamido)-4-phenylbenzoic acid as a light yellow solid.

Workup

  1. stirringby stirring at 50° C. for 30 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-d7b14c02e40d462aa361be3debb93299
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492582B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes