Ethanol → 1-{3-{4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl}propyl}3-(4-cyanophenyl)urea

HRID 1380202ノート

反応式

HRID 1380202 の反応式
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)=[O:7].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:20][CH:19]=1.C(N(CC)CC)C.C(O)C>CCOCC>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][N:27]2[CH2:28][CH2:29][N:30]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=3)=[O:7])[CH2:31][CH2:32]2)=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 702EthanolHCID 8471TriethylamineHCID 1628731-(3-(4-Chlorophenyl)propyl)piperazineHCID 136067331-(3-Chloropropyl)-3-(4-cyanophenyl)urea

生成物 1

HCID 136067281-{3-{4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl}propyl}3-(4-cyanophenyl)urea収率 42%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 1-(3-chloropropyl)-3-(4-cyanophenyl)urea (3.57 g; 15 mmole), 1-[3-(4-chlorophenyl)propyl]piperazine (3.58 g; 15 mmole), triethylamine (1.52 g; 15 mmole), and ethanol (100 ml) was refluxed for 35 hours. The solvent was removed in vacuo and water added to the residue. The product was extracted with ether, dried, and concentrated in vacuo. The resulting reddish-yellow oil was purified on a silica gel column (methylene chloride/methanol 9:1) to give the product as a free base (2.8 g; 42% yield). The product was dissolved in ether and precipitated with ethereal hydrochloric acid to provide, after recrystallization from water, the title compound as colorless crystals, m.p. 219°-221° C.

後処理

  1. temperaturewas refluxed for 35 hours
  2. customThe solvent was removed in vacuo and water
  3. additionadded to the residue
  4. extractionThe product was extracted with ether
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe resulting reddish-yellow oil was purified on a silica gel column (methylene chloride/methanol 9:1)
  8. customto give the product as a free base (2.8 g; 42% yield)
  9. customprecipitated with ethereal hydrochloric acid
  10. customto provide
  11. customafter recrystallization from water

出典と根拠

ORDレコード
ord-ce57af3d83a3486687082a4cdfe226f2
出典データセット
uspto-grants-1986_04
特許番号
US04579947

反応ノート

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