Sodium Carbonate → Ethyl 4-[2-[1-(6-butyl-3-pyridazinyl)-4-piperidinyl]ethoxy]benzoate

HRID 981650Notes

Reaction equation

HRID 981650 reaction equation
[CH2:1]([C:5]1[N:6]=[N:7][C:8](Cl)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][O:20][C:21]2[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=2)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>O.ClCCl>[CH2:1]([C:5]1[N:6]=[N:7][C:8]([N:12]2[CH2:13][CH2:14][CH:15]([CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:30][CH:31]=3)[CH2:16][CH2:17]2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 14989200Ethyl 4-[2-(4-piperidinyl)ethoxy]benzoateHCID 149893013-Butyl-6-chloropyridazine

Product 1

HCID 14989308Ethyl 4-[2-[1-(6-butyl-3-pyridazinyl)-4-piperidinyl]ethoxy]benzoateYield 20.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2.4 parts of 3-butyl-6-chloropyridazine, 4.2 parts of ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate and 2.1 parts of sodium carbonate was stirred for 4 hours at 140° C. After cooling, the reaction mixture was taken up in water and dichloromethane. The separated organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off, washed with 2,2'-oxybispropane and dried at 50° C., yielding 1.2 parts (20.8%) of ethyl 4-[2-[1-(6-butyl-3-pyridazinyl)-4-piperidinyl]ethoxy]benzoate; mp. 91.4° C. (comp. 84).

Workup

  1. temperatureAfter cooling
  2. customThe separated organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 2,2'-oxybispropane
  10. filtrationThe product was filtered off
  11. washwashed with 2,2'-oxybispropane
  12. customdried at 50° C.

Sources & evidence

ORD record
ord-76928e7bd9144790a749623dde1584a9
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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