Ammonium Hydroxide → 3-(4-Ethylphenoxy)-6-[4-(3-methylphenyl)-1-piperazinyl]pyridazine
Reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:19]=[C:20]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:21]=[CH:22][CH:23]=1.[OH-].[NH4+]>ClC(Cl)Cl>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]2[N:6]=[N:7][C:2]([N:27]3[CH2:28][CH2:29][N:24]([C:20]4[CH:21]=[CH:22][CH:23]=[C:18]([CH3:17])[CH:19]=4)[CH2:25][CH2:26]3)=[CH:3][CH:4]=2)=[CH:10][CH:11]=1)[CH3:16]Participants
5
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 4 parts of 6-chloro-3-(4-ethylphenoxy)pyridazine and 6 parts of 1-(3-methylphenyl)piperazine was stirred and heated for 3 hours in an oil bath at 110° C. The whole was alloWed to stand overnight. Concentrate ammonium hydroxide and trichloromethane were added. The precipitate was filtered off and the filtrate was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 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 and dried, yielding 1.7 parts (27%) of 3-(4-ethylphenoxy)-6-[4-(3-methylphenyl)-1-piperazinyl]pyridazine; mp. 106.6° C. (compound 221).
Workup
- filtrationThe precipitate was filtered off
- customthe filtrate was purified by column chromatography over silica gel using
- additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
- customThe pure fractions were collected
- customthe eluent was evaporated
- customThe residue was crystallized from 2,2'-oxybispropane
- filtrationThe product was filtered off
- customdried
Sources & evidence
- ORD record
- ord-df627013c6d34e0b8b6a218a80ad02e3
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05001125
Reaction notes
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