Thionyl Chloride → HCID 53771289, compound
Reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=2)[CH2:9][CH2:8]1.[C:28]1([NH2:39])C(F)=C(F)C(F)=C(N)[C:29]=1F.Cl.Cl.S(Cl)(Cl)=[O:43]>>[OH:43][CH2:29][CH2:28][NH:39][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][C:15]([CH2:14][CH2:13][N:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:24]=[CH:25][CH:26]=[CH:27][C:4]=3[Cl:3])[CH2:8][CH2:9]2)=[CH:16][CH:17]=1Participants
4
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 11.0 g. (24.4 mmole) 4-{2-[1-(2-chlorobenzyl)-piperazin-4-yl]-ethyl}-benzoyl chloride dihydrochloride (prepared from the dihydrochloride of the acid by boiling for 3 hours with excess thionyl chloride, evaporating and digesting with ligroin; yield 98% of theory; m.p. 260° C.) and 10 ml. anhydrous pyridine there are added, with stirring at 20° C., 10 ml. ethanolamine and the reaction mixture is left to stand overnight and then poured into about 100 ml. water. The precipitate obtained is washed with an aqueous solution of sodium bicarbonate and with water, dried and then recrystallised from aqueous ethanol. There is obtained a yield of the desired product of 5.0 g. (51% of theory); m.p. 121°-122° C.
Workup
- customevaporating
- additionanhydrous pyridine there are added
- waitethanolamine and the reaction mixture is left
- additionpoured into about 100 ml
- customThe precipitate obtained
- washis washed with an aqueous solution of sodium bicarbonate and with water
- customdried
- customrecrystallised from aqueous ethanol
Sources & evidence
- ORD record
- ord-cbda4eafbef14c6e8661c560c63889aa
- Source dataset
- uspto-grants-1986_10
- Patent number
- US04616086
Reaction notes
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