Sodium Iodide → HCID 6426406, compound

HRID 1279424Notes

Reaction equation

HRID 1279424 reaction equation
Cl.Cl[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]Cl.[I-].[Na+].[CH2:11]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CO>[CH2:11]([N:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:25]=[CH:26][C:27]([N:28]3[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]3)=[CH:29][CH:30]=2)[CH2:22][CH2:23]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 7372594-(4-Benzylpiperazin-1-yl)aniline

Product 1

HCID 6426406HCID 6426406, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Bis(2-chloroethyl)amine hydrochloride (534 mg; 3.0 mmol) and sodium iodide (3.0 g; 20 mmol) were added to a solution in methanol (20 ml) of 4-(4-benzyl-1-piperazinyl)-aniline (1.1 g; 4.1 mmol) synthesized by the above process, and the mixture was stirred for 13 hours in a bath controlled at 70° C. The reaction mixture was concentrated under reduced pressure, and a 5% aqueous solution of sodium hydrogencarbonate was added to the resultant concentrated residue to conduct extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 775 mg of impurity-containing 4-(4-benzyl-1-piperazinyl)-1-(1piperazinyl)benzene as an oil. Trimethylamine (0.3 ml; 2.2 mmol) and di-tert-butyl dicarbonate (450 mg; 2.1 mmol) were added to a solution of this oil (775 mg) in methylene chloride (5 ml) under ice cooling, and the mixture was stirred for 30 minutes. A saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture to conduct extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining crude crystals (738 mg; yield: 42%) of 4-(4-benzyl-1-piperazinyl)-1-(4-tert-butoxycarbonyl-1-piperazinyl)-benzene. The crude crystals were recrystallized from chloroform-diethyl ether-n-hexane to obtain colorless flakes (melting point: 132-133° C.).

Workup

  1. customsynthesized by the above process
  2. customcontrolled at 70° C
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiona 5% aqueous solution of sodium hydrogencarbonate was added to the resultant concentrated residue
  5. extractionextraction with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1362130e7b6545e7b7fcf41e8b57201e
Source dataset
uspto-grants-2002_09
Patent number
US06448242B1

Reaction notes

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