Potassium Carbonate → HCID 66990822, compound

HRID 454655Notes

Reaction equation

HRID 454655 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH2:14]([O:21][C:22]1[CH:49]=[CH:48][C:47]([O:50][CH2:51][CH2:52]Br)=[CH:46][C:23]=1[C:24]([NH:26][C:27]1[CH:39]=[C:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:37]=[CH:36][C:28]=1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC(C)=O>[CH2:14]([O:21][C:22]1[CH:49]=[CH:48][C:47]([O:50][CH2:51][CH2:52][N:11]2[CH2:12][CH2:13][N:8]([CH3:7])[CH2:9][CH2:10]2)=[CH:46][C:23]=1[C:24]([NH:26][C:27]1[CH:39]=[C:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:37]=[CH:36][C:28]=1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 531671-Methylpiperazine2×HCID 66990269HCID 66990269, compound

Product 1

HCID 66990822HCID 66990822, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (1.0 g) and 1-methylpiperazine (0.83 mL) were added to an acetone (7.5 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate (1.5 g), followed by heating to reflux for 2 hours. The reaction mixture was cooled to room temperature, and potassium carbonate (0.34 g) and 1-methylpiperazine (0.28 mL) were added thereto, followed by heating to reflux for 2 hours. After cooling the reaction mixture to room temperature, the solvent was evaporated under reduced pressure, and water and chloroform were added to the residue. The organic layer was separated, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-95% chloroform/methanol] to obtain tert-butyl 2-(2-(benzyloxy)-5-(2-(4-methylpiperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 2 hours
  3. temperatureby heating
  4. temperatureto reflux for 2 hours
  5. temperatureAfter cooling the reaction mixture to room temperature
  6. customthe solvent was evaporated under reduced pressure, and water and chloroform
  7. additionwere added to the residue
  8. customThe organic layer was separated
  9. customthe solvent was removed under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-95% chloroform/methanol]

Sources & evidence

ORD record
ord-31b59f62ddd64f128e756b12f736797e
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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