Hydrochloric Acid → 1H-Indole, 7-(1-piperazinyl)-

HRID 1779341ノート

反応式

HRID 1779341 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.Cl.Cl[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]Cl.C(=O)([O-])[O-].[K+].[K+].Cl>C(O)CCC>[N:1]1([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:10]=2[NH:9][CH:8]=[CH:7]3)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2 回HCID 1116347-AminoindoleHCID 522769Bis(2-chloroethyl)amine hydrochloride2 回

生成物 1

HCID 30695021H-Indole, 7-(1-piperazinyl)-収率 32.3%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

A suspension of 7-aminoindole (4.10 g, 0.031 moles), bischloroethylamine hydrochloride (6.23 g, 0.035 moles) and potassium carbonate (9.66 g, 0.035 moles) in butanol (100 ml) was heated at reflux under argon for 6h. Further bischloroethylamine hydrochloride (3.0 g, 0.016 moles) and potassium carbonate (4.5 g, 0.016 moles) was added, then the suspension was heated at reflux under argon for 18 h. The solvent was evaporated in vacuo to give a deep purple residue which was taken up into dilute hydrochloric acid (300 ml), washed with ethyl acetate (2×100 ml), made basic with sodium hydroxide, extracted into dichloromethane, filtered, dried (MgSO4) then evaporated in vacuo to a yellow oil. This was crystallised twice from ether to give 7-(1-piperazinyl)indole (2.07 g, 0.010 moles) as a grey/white solid.

後処理

  1. temperaturewas heated
  2. temperatureat reflux under argon for 6h
  3. temperaturethe suspension was heated
  4. temperatureat reflux under argon for 18 h
  5. customThe solvent was evaporated in vacuo
  6. customto give a deep purple residue which
  7. washwashed with ethyl acetate (2×100 ml)
  8. extractionextracted into dichloromethane
  9. filtrationfiltered
  10. dry with materialdried (MgSO4)
  11. customthen evaporated in vacuo to a yellow oil
  12. customThis was crystallised twice from ether

出典と根拠

ORDレコード
ord-fc573b3e8e344d1bb25c612aa37caafe
出典データセット
uspto-grants-1997_05
特許番号
US05627177

反応ノート

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