1-Methylpiperazine → Tert-butyl 2-(2-(methoxymethoxy)-5-((4-methylpiperazin-1-yl)methyl)benzamido)-4-phenylbenzoate

HRID 454643Notes

Reaction equation

HRID 454643 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:38][CH2:39][O:40][CH3:41])=[C:14]([CH:37]=1)[C:15]([NH:17][C:18]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][C:19]=1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:16]>CC(C)=O>[CH3:41][O:40][CH2:39][O:38][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:37][C:14]=1[C:15]([NH:17][C:18]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][C:19]=1[C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])=[O:16]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 66990849Tert-butyl 2-(5-(bromomethyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 66990856Tert-butyl 2-(2-(methoxymethoxy)-5-((4-methylpiperazin-1-yl)methyl)benzamido)-4-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under ice-cooling, 1-methylpiperazine (0.16 mL) was added to an acetone (2.3 mL) suspension of tert-butyl 2-(5-(bromomethyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate (0.15 g), followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and a 1.0 mol/L aqueous solution of sodium hydroxide and chloroform were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium 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: 100-95% chloroform/methanol] to obtain 0.14 g of tert-butyl 2-(2-(methoxymethoxy)-5-((4-methylpiperazin-1-yl)methyl)benzamido)-4-phenylbenzoate as a yellow oil substance.

Workup

  1. temperatureUnder ice-cooling
  2. customThe solvent was evaporated under reduced pressure
  3. additiona 1.0 mol/L aqueous solution of sodium hydroxide and chloroform were added to the residue
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-95% chloroform/methanol]

Sources & evidence

ORD record
ord-87ab3855dc134a15bac98f2976ea2aef
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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