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

HRID 1112742
ノート
印刷プレビュー

反応式

HRID 1112742 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241
Benzene
溶媒
2 回
HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fcb00965ee9b40618a16ee9886e1f16a
出典データセット
uspto-grants-1978_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04123529

反応ノート

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