Chloroform → Tert-butyl 2-(5-(4-(dimethylamino)piperidin-1-yl)-2-hydroxybenzamido)-4-phenylbenzoate

HRID 454605Notes

Reaction equation

HRID 454605 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][CH:40]([N:43]([CH3:45])[CH3:44])[CH2:39][CH2:38]2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])C1C=CC=CC=1.C(Cl)(Cl)Cl>CO.C(OCC)(=O)C.[C].[Pd]>[CH3:45][N:43]([CH3:44])[CH:40]1[CH2:39][CH2:38][N:37]([C:34]2[CH:35]=[CH:36][C:9]([OH:8])=[C:10]([CH:33]=2)[C:11]([NH:13][C:14]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:24]=[CH:23][C:15]=2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])[CH2:42][CH2:41]1

Participants

6

Reactant 2

HCID 6212ChloroformHCID 66989971Tert-butyl 2-(2-(benzyloxy)-5-(4-(dimethylamino)piperidin-1-yl)benzamido)-4-phenylbenzoate

Product 1

HCID 58508796Tert-butyl 2-(5-(4-(dimethylamino)piperidin-1-yl)-2-hydroxybenzamido)-4-phenylbenzoateYield 59.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-(4-(dimethylamino)piperidin-1-yl)benzamido)-4-phenylbenzoate (0.13 g) in methanol (1.5 mL) and ethyl acetate (1.5 mL), 10% palladium-carbon (0.13 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. Chloroform was added to the reaction mixture, and the insoluble substance was removed by filtration. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-90% chloroform/methanol] to obtain 0.066 g of tert-butyl 2-(5-(4-(dimethylamino)piperidin-1-yl)-2-hydroxybenzamido)-4-phenylbenzoate.

Workup

  1. additionwas added
  2. customthe insoluble substance was removed by filtration
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-ed08bc0d4d1d42e8b2eb760ac4619f06
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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