Acetic Acid → 7,7-Difluoro-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

HRID 1843206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1843206
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[CH2:11][C:10]([F:14])([F:13])[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]1[C:15]([O:17]CC)=O.C(O)(=O)C>C1(C)C=CC=CC=1>[F:13][C:10]1([F:14])[CH2:11][C:12]2[N:4]3[CH2:3][CH2:2][NH:1][C:15](=[O:17])[C:5]3=[CH:6][C:7]=2[CH2:8][CH2:9]1

Komponenten

4

Edukt 2

HCID 176Acetic AcidHCID 86683733Ethyl 1-(2-Aminoethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Produkt 1

HCID 866837357,7-Difluoro-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-oneAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Into a 250-mL round-bottom flask was placed a solution of 113n (10 g, 36.73 mmol, 1.00 equiv) in toluene (100 mL) and acetic acid (1.1 g, 18.32 mmol, 0.50 equiv). See FIG. 14. The resulting solution was heated to reflux for 2 h, cooled and concentrated under vacuum. The residue was triturated in 100 mL of dry ether. The crude product was purified by recrystallization from ethanol to afford 4.43 g (53%) of 113o as a white solid. MS-ESI: [M+H]+ 227. 1H NMR (300 MHz, DMSO) δ 2.10-2.24 (2H, m), 2.59-2.64 (2H, m), 3.17-3.27 (2H, m), 3.43-3.48 (2H, m), 3.88-3.92 (2H, m), 6.44 (1H, s), 7.56 (1H, s).

Aufarbeitung

  1. customInto a 250-mL round-bottom flask was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 2 h
  4. temperaturecooled
  5. concentrationconcentrated under vacuum
  6. customThe residue was triturated in 100 mL of dry ether
  7. customThe crude product was purified by recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4dbe10da3d754baab46c1174f76007dc
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946213B2

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