Potassium Carbonate → Tert-butyl 2-(2-(methoxymethoxy)-5-((4-propylpiperazin-1-yl)methyl)benzamido)-4-phenylbenzoate

HRID 454644Notes

Reaction equation

HRID 454644 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:37][CH2:38][O:39][CH3:40])=[C:13]([CH:36]=1)[C:14]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:15].Cl.Cl.[CH2:43]([N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1)[CH2:44][CH3:45]>CC(C)=O>[CH3:40][O:39][CH2:38][O:37][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:49]2[CH2:50][CH2:51][N:46]([CH2:43][CH2:44][CH3:45])[CH2:47][CH2:48]2)=[CH:36][C:13]=1[C:14]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 534225931-PropylpiperazineHCID 66990849Tert-butyl 2-(5-(bromomethyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 66990553Tert-butyl 2-(2-(methoxymethoxy)-5-((4-propylpiperazin-1-yl)methyl)benzamido)-4-phenylbenzoateYield 67.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under ice-cooling, potassium carbonate (0.19 g) and tert-butyl 2-(5-(bromomethyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate (0.12 g) were sequentially added to an acetone (1.8 mL) suspension of 1-propylpiperazine dihydrochloride (0.13 g), followed by stirring at room temperature for 5 hours and 30 minutes. The solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue. The organic layer was separated and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. 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 0.088 g of tert-butyl 2-(2-(methoxymethoxy)-5-((4-propylpiperazin-1-yl)methyl)benzamido)-4-phenylbenzoate.

Workup

  1. temperatureUnder ice-cooling
  2. customThe solvent was evaporated under reduced pressure
  3. additiona saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. 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-50a659d59bc64a82a63b2af7939a028d
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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