Potassium Carbonate → HCID 66990342, compound

HRID 454637Notes

Reaction equation

HRID 454637 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8]([O:15][C:16]1[CH:43]=[CH:42][C:41]([CH2:44][CH2:45]Br)=[CH:40][C:17]=1[C:18]([NH:20][C:21]1[CH:33]=[C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:30][C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:8]([O:15][C:16]1[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:40][C:17]=1[C:18]([NH:20][C:21]1[CH:33]=[C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:30][C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 531671-Methylpiperazine2×HCID 66990392HCID 66990392, compound

Product 1

HCID 66990342HCID 66990342, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under ice-cooling, 1-methylpiperazine (0.095 mL) was addedd to an acetone (1.5 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-(2-bromoethyl)benzamido)-4-phenylbenzoate (0.10 g), followed by stirring at room temperature for 30 minutes. Potassium carbonate (0.035 g) was added thereto, followed by stirring at room temperature for 1 hour. 1-Methylpiperazine (0.095 mL) and potassium carbonate (0.035 g) were added to the reaction mixture, followed by stirring at room temperature for 1 hour. The reaction mixture was left to stand overnight. The solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.10 g of tert-butyl 2-(2-(benzyloxy)-5-(2-(4-methylpiperazin-1-yl)ethyl)benzamido)-4-phenylbenzoate.

Workup

  1. temperatureUnder ice-cooling
  2. stirringby stirring at room temperature for 1 hour
  3. stirringby stirring at room temperature for 1 hour
  4. waitThe reaction mixture was left
  5. waitto stand overnight
  6. customThe solvent was evaporated under reduced pressure
  7. additiona saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue
  8. customThe organic layer was separated
  9. washwashed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-6acd517c8be84221ae6c85d3c458244d
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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