Hydrochloric Acid → HCID 22558210, compound

HRID 2270966Notes

Reaction equation

HRID 2270966 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]2[O:9][C:8]([N:10]3[CH2:17][CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:7][C:6]=2[CH:18]=1.[CH2:20]=O.Cl.[H][H]>CO.[C].[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]2[O:9][C:8]([N:10]3[CH2:17][CH2:16][CH2:15][CH2:14][N:13]([CH3:20])[CH2:12][CH2:11]3)=[N:7][C:6]=2[CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 22558197HCID 22558197, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22558210HCID 22558210, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

5,7-Dimethyl-2-(1,4-diazacyclooctanyl)benzoxazole (135 mg) was dissolved in methanol (3 ml), and the solution was mixed with 37% formaldehyde solution (1 ml) and 1 N hydrochloric acid (0.5 ml). This was further mixed with 10% palladium-carbon (10 mg) and stirred overnight in an atmosphere of hydrogen. After removing the catalyst by celite filtration, the filtrate was washed with ethyl acetate and then the solvent was evaporated. The thus obtained residue was extracted with 1 N hydrochloric acid and ethyl acetate, and the resulting water layer was adjusted to pH 8 with potassium carbonate and extracted with methylene chloride. The organic layer was dried with magnesium sulfate and the solvent was evaporated to obtain the title compound 5,7-dimethyl-2-(4-methyl-1,4-diazacyclooctanyl)benzoxazole (50 mg).

Workup

  1. customAfter removing the catalyst
  2. filtrationby celite filtration
  3. washthe filtrate was washed with ethyl acetate
  4. customthe solvent was evaporated
  5. extractionThe thus obtained residue was extracted with 1 N hydrochloric acid and ethyl acetate
  6. extractionextracted with methylene chloride
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-aa96a589040443498cae50f55c9c4eec
Source dataset
uspto-grants-2001_12
Patent number
US06333328B1

Reaction notes

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