Hydrochloric Acid → HCID 68669747, Verbindung

HRID 2389857

Reaktionsgleichung

Reaktionsgleichung von HRID 2389857
[Cl:1][C:2]1[C:11]2[C:12]3[C:17]([NH:18][C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3.N1C2C(=CC=CC=2)C(=O)C1=O.[NH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.Cl>C(OCCO)C.C(OCC)(=O)C.CO>[ClH:1].[CH:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[C:10]1[NH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=1[C:2]([NH:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)=[N:3]2

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 7054IsatinHCID 8795AminoethylpiperazineHCID 54103076-Chloro-11H-indolo[3,2-c]quinoline

Produkt 1

HCID 68669747HCID 68669747, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8076Glycol monoethyl etherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of compound 4a as obtained from the above Synthesis Ex. 1 (1.26 g, 5 mmol) and 1-(2-aminoethyl)piperazine (1.94 g, 15 mmol) in 2-ethoxyethanol (50 mL) was heated at 140-150° C. for 48 hrs (by TLC monitoring). After cooling, the reaction mixture was evaporated in vacuo to give a residue, which was dissolved in ethyl acetate (EA) (50 mL). The EA layer was washed with H2O and brine, and then dried on MgSO4. Concentration of the EA layer gave a residue, which was dissolved in MeOH (10 mL), followed by addition of a solution of 6N HCl at 0° C. The resultant mixture was stirred at room temperature for 8 hrs to result in precipitation, followed by filtration. The precipitate thus collected was washed with MeOH and then dried at 90° C. under reduced pressure for 24 hrs to give N-(11H-indolo[3,2-c]quinolin-6-yl)-2-(piperazin-1-yl)ethanamine hydrochloride, which was purified by flash column chromatography (FCC) (silica gel; MeOH/CH2Cl2=1/10 to 1/3) to give the title compound 5 as an orange color powder (0.51 g, 29% yield).

Aufarbeitung

  1. customas obtained from the above Synthesis Ex
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated in vacuo
  4. customto give a residue, which
  5. washThe EA layer was washed with H2O and brine
  6. customdried on MgSO4
  7. customConcentration of the EA layer gave a residue, which
  8. customto result in precipitation
  9. filtrationfollowed by filtration
  10. customThe precipitate thus collected
  11. washwas washed with MeOH
  12. customdried at 90° C. under reduced pressure for 24 hrs

Quellen und Nachweise

ORD-Eintrag
ord-64e715524fce48cf9f06e62038db86a3
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273760B2

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