Dimethylformamide → Ethyl 4-[2-[1-(6-fluoro-3-pyridazinyl)-4-piperidinyl]ethoxy]benzoate

HRID 484511Notes

Reaction equation

HRID 484511 reaction equation
F[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[NH:3]1.C(O)(=O)CCC(O)=O.[NH:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][O:25][C:26]2[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=2)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[F:8][C:4]1[N:3]=[N:2][C:7]([N:17]2[CH2:18][CH2:19][CH:20]([CH2:23][CH2:24][O:25][C:26]3[CH:27]=[CH:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:35][CH:36]=3)[CH2:21][CH2:22]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 197482732,6-DifluoropyridazineHCID 23056112Ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate butanedioate

Product 1

HCID 14989295Ethyl 4-[2-[1-(6-fluoro-3-pyridazinyl)-4-piperidinyl]ethoxy]benzoateYield 64.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture 1.2 parts of 2,6-difluoropyridazine, 4 parts of ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate butanedioate(1:1), 5.3 parts of sodium carbonate and 141 parts of N,N-dimethylformamide was stirred for 48 hours at 60° C. After cooling, the reaction mixture was poured into water. The precipitated product was filtered off, washed with water and dissolved in trichloromethane. The organic layer was dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 2.4 parts (64.3%) of ethyl 4-[2-[1-(6-fluoro-3-pyridazinyl)-4-piperidinyl]ethoxy]benzoate; mp. 131.9° C. (comp. 73).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitated product was filtered off
  3. washwashed with water
  4. dissolutiondissolved in trichloromethane
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from 2-propanol
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-f656ffe6358e40279ae012832786cd0c
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

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