Sodium Carbonate → Ethyl 4-[3-[1-[6-(4-fluorophenyl)-3-pyridazinyl]-4-piperidinyl]propoxy]benzoate

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Reaktionsgleichung

Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:4]=[N:3][C:2]([N:15]3[CH2:16][CH2:17][CH:18]([CH2:21][CH2:22][CH2:23][O:24][C:25]4[CH:26]=[CH:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:34][CH:35]=4)[CH2:19][CH2:20]3)=[CH:7][CH:6]=2)=[CH:9][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

A mixture of 2.1 parts of 3-chloro-6-(4-fluorophenyl)pyridazine, 2.9 parts of ethyl 4-[3-(4-piperidinyl)propoxy]benzoate, 1.1 parts of sodium carbonate and 2 parts of N,N-dimethylacetamide was stirred for 2 hours in an oil bath at 140° C. The reaction mixture was diluted with water while cooling. 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 3.4 parts (73.3%) of ethyl 4-[3-[1-[6-(4-fluorophenyl)-3-pyridazinyl ]-4-piperidinyl]propoxy]benzoate; mp. 160.4° C. (comp. 81).

Aufarbeitung

temperaturewhile cooling
filtrationThe precipitated product was filtered off
washwashed with water
dissolutiondissolved in trichloromethane
customThe organic layer was dried
filtrationfiltered
customevaporated
customThe residue was crystallized from 2-propanol
filtrationThe product was filtered off
customdried

Quellen und Nachweise

ORD-Eintrag: ord-319338032bea49329ef100e66a35de90
Quelldatensatz: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05231184

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