Sodium Carbonate → HCID 15045179, compound

HRID 1614333Notes

Reaction equation

HRID 1614333 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[CH2:6][CH2:5]1.[CH2:17]([C:19]1[O:23][N:22]=[C:21]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[N:20]=1)[CH3:18].C(=O)([O-])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[CH2:17]([C:19]1[O:23][N:22]=[C:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:2][CH2:3][CH:4]3[CH2:9][CH2:8][N:7]([C:10]4[N:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=4)[CH2:6][CH2:5]3)=[CH:26][CH:25]=2)[N:20]=1)[CH3:18]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 149892183-[4-(2-Chloroethyl)-1-piperidinyl]-6-methylpyridazineHCID 135760587HCID 135760587, compound

Product 1

HCID 15045179HCID 15045179, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3.12 parts of 3-[4-(2-chloroethyl)-1-piperidinyl]-6-methylpyridazine, 2.47 parts of 4-(5-ethyl-1,2,4-oxadiazol-3-yl)phenol, 1.38 parts of sodium carbonate and 94 parts of N,N-dimethylacetamide was stirred overnight at 110° C. After cooling, the reaction mixture was poured into water. The precipitate was filtered off, washed with water and dissolved in trichloromethane. This solution was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 97:3). The eluent of the desired fraction was evaporated and the residue was crystallized from 2-propanone. The product was filtered off and dried, yielding 1.7 parts (33.2%) of 3-[4-[2-[4-(5-ethyl-1,2,4-oxadiazol-3-yl)phenoxy]ethyl]-1-piperidinyl]-6-methylpyridazine; mp. 125.3° C. (comp. 6).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. dissolutiondissolved in trichloromethane
  5. customThis solution was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 97:3)
  9. customThe eluent of the desired fraction was evaporated
  10. customthe residue was crystallized from 2-propanone
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-5c2dc07b18574e46b623f30546428eb0
Source dataset
uspto-grants-1993_03
Patent number
US05196535

Reaction notes

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