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

HRID 1779341Notes

Reaction equation

HRID 1779341 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fc573b3e8e344d1bb25c612aa37caafe
Source dataset
uspto-grants-1997_05
Patent number
US05627177

Reaction notes

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