Diisopropylethylamine → HCID 71252181, compound

HRID 2411226

Reaction equation

HRID 2411226 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C.Cl[CH2:20][CH2:21][N:22]([CH2:33][CH2:34]Cl)[S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>O>[CH3:9][C:3]1[CH:4]=[C:5]([CH3:8])[N:6]=[CH:7][C:2]=1[N:1]1[CH2:34][CH2:33][N:22]([S:23]([C:26]2[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=2)(=[O:25])=[O:24])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 70606694,6-Dimethylpyridin-3-amine

Product 1

HCID 71252181HCID 71252181, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5-amino-2,4-dimethylpyridine (883 mg) were added N,N-diisopropylethylamine (2.1 mL) and N,N-bis(2-chloroethyl)-p-toluenesulfonamide (2.08 g), and the mixture was stirred with heating under reflux. After completion of the reaction, water was added to the reaction mixture, the mixture was extracted with chloroform, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give 1-(4,6-dimethylpyridin-3-yl)-4-(toluene-4-sulfonyl)piperazine (380 mg). The obtained 1-(4,6-dimethylpyridin-3-yl)-4-(toluene-4-sulfonyl)piperazine (380 mg) was dissolved in acetic acid (2 mL), 40% hydrobromic acid (2 mL) was added, and the mixture was stirred at 100° C. After completion of the reaction, the reaction mixture was neutralized with aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The solvent was evaporated from the organic layer to give the title compound (131 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with chloroform
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-eb0674f3edd244f3995b85e2b604a5a1
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Linked notes

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