Triethylamine → Piperazine,1-(3-bromophenyl)-4-[[5-(4-chlorophenyl)-2-furanyl]carbonyl]-

5-(4-Chlorophenyl)-2-furoic acid (Australian Journal of Chemistry, 26, 1147 (1973))(6.67 g; 0.03 mole) was refluxed in benzene (100 ml) with thionyl chloride (4.5 ml) for 1.5 hours. After removal of the excess thionyl chloride, the remaining acid chloride in benzene was added dropwise with stirring and cooling to a mixture of N-(3-bromophenyl)-piperazine (7.23 g; 0.03 mole) and triethylamine (4.5 ml, ca. 0.03 mole) in benzene (100 ml). After stirring for 1 hour at room temperature, the mixture was shaken with water (100 ml). The separated benzene phase was further washed with saturated salt solution, then evaporated to give an oil which readily crystallised. The product was recrystallised from ethyl acetate/60°-80° C. petroleum ether (1/3 v /v) to yield 1-[5-(4-chlorophenyl)-2-furoyl]-4-(3-bromophenyl)-piperazine (12.3 g) m.p. 130° C.

1. customAfter removal of the excess thionyl chloride
2. additionthe remaining acid chloride in benzene was added dropwise
3. stirringAfter stirring for 1 hour at room temperature
4. washThe separated benzene phase was further washed with saturated salt solution
5. customevaporated
6. customto give an oil which
7. customreadily crystallised
8. customThe product was recrystallised from ethyl acetate/60°-80° C. petroleum ether (1/3 v /v)

ORD record

ord-fcb00965ee9b40618a16ee9886e1f16a

Source dataset

uspto-grants-1978_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04123529