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

HRID 1112742
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HRID 1112742 반응식
[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
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참가 물질

7

반응물 4

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

생성물 1

HCID 22762644Piperazine,1-(3-bromophenyl)-4-[[5-(4-chlorophenyl)-2-furanyl]carbonyl]-수율 92%

시약·촉매·용매 2

HCID 241
Benzene
용매
2회
HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fcb00965ee9b40618a16ee9886e1f16a
출처 데이터셋
uspto-grants-1978_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04123529

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