1-Aminopiperazine → Piperazin-1-yl-(5-chlorobenzofuran-2-yl methylene)amine

HRID 856056Notes

Reaction equation

HRID 856056 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]=O)=[CH:14][C:13]=2[CH:19]=1>C(O)(C)C>[N:2]1([N:1]=[CH:17][C:15]2[O:16][C:12]3[CH:11]=[CH:10][C:9]([Cl:8])=[CH:19][C:13]=3[CH:14]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 1473921-AminopiperazineHCID 134001705-Chloro-1-benzofuran-2-carbaldehyde

Product 1

HCID 69481679Piperazin-1-yl-(5-chlorobenzofuran-2-yl methylene)amineYield 98.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-Aminopiperazine (29 g, 287 mmol) was dissolved in isopropyl alcohol (173 ml), to which 5-chlorobenzofuran-2-aldehyde (34.52 g, 191 mmol) was added, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to afford piperazin-1-yl-(5-chlorobenzofuran-2-yl methylene)amine (49.49 g, yield 98%) as a yellow crystalline powder.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-06e71284de14429ca218e5eee2180f5e
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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