Sodium Carbonate → HCID 10928314, compound

HRID 129751Notes

Reaction equation

HRID 129751 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23][N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34].C(=O)([O-])[O-].[Na+].[Na+]>[I-].[Na+].C(C(C)=O)C(C)C>[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][CH2:23][N:24]3[C:28](=[O:29])[C:27]4=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]4[C:25]3=[O:34])[CH2:12][CH2:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 70048Benzhydrylpiperazine

Product 1

HCID 10928314HCID 10928314, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 500 mg (1.98 mmole) of 4-(diphenylmethyl)piperazine, 530 mg (1.98 mmole) of N-(3-bromopropyl)phthalimide, 840 mg (7.92 mmole) of sodium carbonate, 10 mg of sodium iodide and 12 ml of methyl isobutyl ketone was heated under reflux overnight. The reaction mixture was then filtered, and the solvent was removed from the filtrate by evaporation under reduced pressure. The resulting residue was subjected to column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to afford 830 mg (yield 96%) of the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. filtrationThe reaction mixture was then filtered
  4. customthe solvent was removed from the filtrate by evaporation under reduced pressure
  5. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-3e27644b42274d7aa61a51ca07e5691a
Source dataset
uspto-grants-1995_11
Patent number
US05470851

Reaction notes

Loading…