Sodium Carbonate → Ethyl 4-[3-[1-[6-(4-fluorophenyl)-3-pyridazinyl]-4-piperidinyl]propoxy]benzoate
Reaction equation
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]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
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).
Workup
- 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
Sources & evidence
- ORD record
- ord-7585ad6094924bf3a44a87f19bbd59f4
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04992433
Reaction notes
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