Dichloromethane → 2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethanamine dihydrochloride

HRID 1071069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071069
[NH2:1][CH2:2][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.C(Cl)[Cl:33]>>[ClH:33].[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][CH2:2][NH2:1])[C:5]=2[CH2:17][CH2:16][NH:15][CH2:14]1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22396663tert-butyl 6-(2-aminoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Produkt 1

HCID 223967722-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethanamine dihydrochloride

Versuchsvorschrift

tert-Butyl 6-(2-aminoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0336 g, 0.102 mmol) was dissolved in CH2Cl2 (2 mL) at rt. CF3CO2H (1 mL) was added and the reaction mixture was stirred for 4 h. The reaction mixture was concentrated and the residue was taken up in EtOAc (2 mL). HCl in Et2O (1 N) and MeOH were added and the mixture was concentrated to give crude 2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethanamine dihydrochloride (0.0339 g). 1H NMR (300 MHz, DMF-d7) δ 3.48-3.51, 3.53-3.59, 3.65-3.70, 3.75-3.79, 4.94, 7.27, 7.35, 7.72, 7.91; MS (ESI+) for C14H19N3 m/z 230.2 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionHCl in Et2O (1 N) and MeOH were added
  3. concentrationthe mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-be90567d2e10421b8ca1a6417fe3b8e3
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903090B2

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