Hydrochloric Acid → 1-[5-Chloro-4-(1-methylethyl)amino-3-pyridazinyl]piperazine

HRID 2293757Notes

Reaction equation

HRID 2293757 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([Cl:12])[C:7]=1[NH:8][CH:9]([CH3:11])[CH3:10].[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.Cl>C1(C)C(C)=CC=CC=1>[Cl:12][C:6]1[C:7]([NH:8][CH:9]([CH3:11])[CH3:10])=[C:2]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[N:3]=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 108221363,5-Dichloro-4-(1-methylethylamino)pyridazine

Product 1

HCID 214776731-[5-Chloro-4-(1-methylethyl)amino-3-pyridazinyl]piperazine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 3,5-dichloro-4-(1-methylethyl)aminopyridazine (PREPARATION 41, 1.77 g) and piperazine (2.96 g) in xylene (18 ml) is refluxed for 40 hr. The mixture is cooled and then treated with concentrated hydrochloric acid (8 ml). After further cooling, a precipitate forms and the organic liquid is separated. The aqueous phase is diluted with an excess of a solution of aqueous sodium hydroxide (10%) and then is extracted with chloroform (3×). The combined organic extracts are washed with water, then saline, dried over sodium sulfate, and concentrated to an oil. The crude product is flash chromatographed on silica gel eluting with methanol. The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 1.20, 3.04, 3.18, 4.46, 4.73 and 8.50 δ; CMR (CDCl3) 24.0, 44.3, 45.9, 50.2, 118.2, 135.8, 148.3 and 155.4 δ.

Workup

  1. temperatureis refluxed for 40 hr
  2. temperatureThe mixture is cooled
  3. temperatureAfter further cooling
  4. customa precipitate forms and the organic liquid is separated
  5. additionThe aqueous phase is diluted with an excess of a solution of aqueous sodium hydroxide (10%)
  6. extractionis extracted with chloroform (3×)
  7. washThe combined organic extracts are washed with water
  8. dry with materialsaline, dried over sodium sulfate
  9. concentrationconcentrated to an oil
  10. customchromatographed on silica gel eluting with methanol
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-23c28f4adb4949fd889a672ed6288880
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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