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

HRID 1030931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1030931
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 14989308Ethyl 4-[2-[1-(6-butyl-3-pyridazinyl)-4-piperidinyl]ethoxy]benzoateAusbeute 20,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

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).

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-67203bf63fb94da98b9dbb99265ed7ef
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106973

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