Hydrochloric Acid → 2-(2,3,4,5-Tetrahydroazepino[4,5-b]indol-6(1h)-yl)acetamide hydrochloride

HRID 1356261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356261
[NH2:1][C:2](=[O:25])[CH2:3][N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]2[CH2:13][CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16][CH2:17][C:5]1=2.C(C(O)=O)(F)(F)F.[ClH:33]>C(Cl)Cl.CCOC(C)=O.CCOCC>[ClH:33].[CH2:13]1[C:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]([CH2:3][C:2]([NH2:1])=[O:25])[C:5]=2[CH2:17][CH2:16][NH:15][CH2:14]1

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 22396556tert-butyl 6-(2-amino-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Produkt 1

HCID 223967072-(2,3,4,5-Tetrahydroazepino[4,5-b]indol-6(1h)-yl)acetamide hydrochlorideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

tert-Butyl 6-(2-amino-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0233 g, 0.0678 mmol) was dissolved in CH2Cl2 (2 mL) at rt. CF3CO2H (0.8 mL) was added, then the reaction mixture was stirred for 30 min. The reaction mixture was concentrated to give a crude product (0.0288 g). The crude product was dissolved in EtOAc (1 mL), 1 N HCl in Et2O (2 mL) was added, and the precipitated salt was collected by filtration. 2-(2,3,4,5-Tetrahydroazepino[4,5-b]indol-6(1H)-yl)acetamide hydrochloride (0.0151 g) was obtained in 80% yield. 1H NMR (300 MHz, DMF-d7) δ 3.29-3.33, 3.40-3.43, 3.50-3.58, 4.97, 7.07, 7.15, 7.45, 7.53; MS (ESI+) for C14H17N3O m/z 244.1 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto give a crude product (0.0288 g)
  3. filtrationthe precipitated salt was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d0ea27dd2c6045459e12ac61d47d2031
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586421B2

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