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Chloroform → Methyl 2-(2-hydroxy-5-(2-(4-propylpiperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate

HRID 454699
Notes
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Reaction equation

HRID 454699 reaction equation
C([O:8][C:9]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH3:45])[CH2:39][CH2:38]2)=[CH:30][C:10]=1[C:11]([NH:13][C:14]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:12])C1C=CC=CC=1.C(Cl)(Cl)Cl>CO.C(OCC)(=O)C.[C].[Pd]>[OH:8][C:9]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]2[CH2:38][CH2:39][N:40]([CH2:43][CH2:44][CH3:45])[CH2:41][CH2:42]2)=[CH:30][C:10]=1[C:11]([NH:13][C:14]1[CH:23]=[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6212ChloroformHCID 66990571Methyl 2-(2-(benzyloxy)-5-(2-(4-propylpiperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 58508918Methyl 2-(2-hydroxy-5-(2-(4-propylpiperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoateYield 62.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst
HCID 887
Methanol
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of methyl 2-(2-(benzyloxy)-5-(2-(4-propylpiperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate (0.081 g) in methanol (1.5 mL) and ethyl acetate (1.5 mL), 10% palladium-carbon (0.081 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours and 30 minutes. Chloroform was added to the reaction mixture. The insoluble substance was removed by filtration, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.043 g of methyl 2-(2-hydroxy-5-(2-(4-propylpiperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate as an orange solid.

Workup

  1. additionwas added
  2. customThe insoluble substance was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. additionDiisopropyl ether was added to the obtained residue
  5. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-df09122cd551431c8f2b12ee79e5b9fc
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492582B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes