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Hydrochloric Acid → 5-Bromo-N-{4-[(1,1-dimethyl)ethyl]-5-piperidinothiazol-2-yl)-2-hydroxybenzamide

HRID 644442
Notes
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Reaction equation

HRID 644442 reaction equation
C([O:4][C:5]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:6]=1[C:7]([NH:9][C:10]1[S:11][C:12]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[N:14]=1)=[O:8])(=O)C.[OH-].[Na+].Cl>C(O)C>[Br:29][C:26]1[CH:27]=[CH:28][C:5]([OH:4])=[C:6]([CH:25]=1)[C:7]([NH:9][C:10]1[S:11][C:12]([N:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)=[C:13]([C:15]([CH3:17])([CH3:18])[CH3:16])[N:14]=1)=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866026812-Acetoxy-5-bromo-N-{4-[(1,1-dimethyl)ethyl)-5-piperidinothiazol-2-yl}benzamide

Product 1

HCID 103658335-Bromo-N-{4-[(1,1-dimethyl)ethyl]-5-piperidinothiazol-2-yl)-2-hydroxybenzamideYield 70.3%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

2-Acetoxy-5-bromo-N-{4-[(1,1-dimethyl)ethyl]-5-piperidinothiazol-2-yl}-benzamide (crude product, 84.3 mg) was dissolved in ethanol (3 mL). 2N Aqueous sodium hydroxide (0.1 mL) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (54.1 mg, 36.3%; 2 steps) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-5ee890246f8042a3acf8d9e87b49d9d5
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700655B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes