Calciumoxide → HCID 14989396, compound

HRID 1030945Notes

Reaction equation

HRID 1030945 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH2:26][CH2:27][N:28]=4)=[CH:20][CH:19]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[O-2].[Ca+2].[H][H]>[Pd].CO>[O:25]1[CH2:26][CH2:27][N:28]=[C:24]1[C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:16][CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:5]3[N:4]=[N:3][CH:2]=[CH:7][CH:6]=3)[CH2:13][CH2:12]2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 6850728CalciumoxideHCID 14989312HCID 14989312, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14989396HCID 14989396, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3.8 parts of 3-chloro-6-[4-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]-1-piperazinyl]pyridazine, 200 parts of methanol and 2 parts of calcium oxide was hydrogenated at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off, washed with 2-propanol and 2,2'-oxybispropane and dried over weekend at 60° C., yielding 0.7 parts (17.2%) of 3-[4-[3-[4-(4,5-dihydro-2 -oxazolyl)phenoxy]propyl]-1-piperazinyl]pyridazine; mp. 144.7° C. (comp. 169).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. extractionthe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from 2-propanol
  12. filtrationThe product was filtered off
  13. washwashed with 2-propanol and 2,2'-oxybispropane
  14. customdried over weekend at 60° C.

Sources & evidence

ORD record
ord-198408ff00f343398e962718036280cc
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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