Sodium Iodide → 1-[3-(Diphenylamino)propyl]-4-(3-fluorophenyl)-4-piperidinol ethanedioate
Reaction equation
[C:1]1([N:7]([CH2:14][CH2:15][CH2:16]Br)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:20]=[C:21]([C:25]2([OH:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1.[C:32](=[O:35])([O-:34])[O-].[Na+].[Na+].[I-].[Na+].C(C(C)=[O:43])C>>[C:25]([OH:31])(=[O:43])[C:32]([OH:34])=[O:35].[C:1]1([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH2:15][CH2:16][N:28]2[CH2:27][CH2:26][C:25]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([F:18])[CH:20]=3)([OH:31])[CH2:30][CH2:29]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Procedure
A mixture of 10.4 g. (0.018 moles) of 3-[N,N-diphenylamino]-1-bromopropane, 3.5 g. (0.018 moles) of 4-(3-fluorophenyl)-4-piperidinol, 1.9 g. (0.018 moles) of sodium carbonate and 1.0 g. of sodium iodide in 100 ml. of methyl ethyl ketone is refluxed for about 3 hours. The reaction is allowed to cool, filtered and the filtrate is evaporated. The residue is shaken with a mixture of diethyl ether and dilute hydrochloric acid. An oily third phase forms which crystallizes on scratching. This material is recrystallized from isopropanol and then from ethanol, and converted back to the free base. The product is then crystallized from isopropanol containing an excess of oxalic acid giving 2.2 g. of 1-[3-(diphenylamino)propyl]-4-(3-fluorophenyl)-4-piperidinol ethanedioate (1:1), mp. 181°-182.5° C.
Workup
- additionA mixture of 10.4 g
- temperatureto cool
- filtrationfiltered
- customthe filtrate is evaporated
- customAn oily third phase forms which crystallizes
- customThis material is recrystallized from isopropanol
- customThe product is then crystallized from isopropanol containing an excess of oxalic acid giving 2.2 g
Sources & evidence
- ORD record
- ord-5242efcf837f40d1816fd3231860f0a6
- Source dataset
- uspto-grants-1982_12
- Patent number
- US04364954
Reaction notes
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