Triethylamine → HCID 22762644, compound

HRID 1112742Notes

Reaction equation

HRID 1112742 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[Br:20][C:21]1[CH:22]=[C:23]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1.C(N(CC)CC)C>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:13]([N:30]3[CH2:29][CH2:28][N:27]([C:23]4[CH:24]=[CH:25][CH:26]=[C:21]([Br:20])[CH:22]=4)[CH2:32][CH2:31]3)=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 7266935-(4-Chlorophenyl)-2-furoic acidHCID 27571541-(3-Bromophenyl)piperazine

Product 1

HCID 22762644HCID 22762644, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fcb00965ee9b40618a16ee9886e1f16a
Source dataset
uspto-grants-1978_10
Patent number
US04123529

Reaction notes

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