Water → HCID 18185391, compound

HRID 1358607Notes

Reaction equation

HRID 1358607 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=2)=[CH:5][N:4]=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.O.C(OCC)(=O)C>C(=O)(O)[O-].[Na+]>[CH3:14][C:12]1([CH3:15])[CH2:11][O:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([N:20]3[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]3)=[N:4][CH:5]=2)=[N:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 531671-MethylpiperazineHCID 18185381HCID 18185381, compound

Product 1

HCID 18185391HCID 18185391, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

2-Chloro-5-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-pyridine hydrochloride was transformed into its free base by dissolving 8.0 g (32 mmol) in saturated sodium bicarbonate solution and extracting the base into dichloromethane. The solvent was evaporated and the residue was dissolved in toluene. After addition of 11.35 g (113 mmol) N-methylpiperazine, the mixture was refluxed for 36 h. After cooling to room temperature water (50 ml) and ethyl acetate (150 ml) were added and the aqueous layer was extracted with ethyl acetate (150 ml). The combined organic layers were extracted two times with 1 N hydrochloric acid, the acidic aqueous layer was made alkaline with 28% sodium hydroxide solution and extracted two times with dichloromethane. The organic layer was dried (magnesium sulfate) and evaporated. The residue was crystallized from ethyl acetate/hexane to yield 6.0 g (67%) of a white crystalline compound.

Workup

  1. extractionextracting the base into dichloromethane
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in toluene
  4. temperaturethe mixture was refluxed for 36 h
  5. additionwere added
  6. extractionthe aqueous layer was extracted with ethyl acetate (150 ml)
  7. extractionThe combined organic layers were extracted two times with 1 N hydrochloric acid
  8. extractionextracted two times with dichloromethane
  9. dry with materialThe organic layer was dried (magnesium sulfate)
  10. customevaporated
  11. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-bba90c51959c4156bf741744ad52b580
Source dataset
uspto-grants-2003_07
Patent number
US06596773B2

Reaction notes

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