Benzo[b]thiophene-3-acetonitrile → Benzo[b]thiophene-3-ethanamine

HRID 228307

Reaktionsgleichung

Reaktionsgleichung von HRID 228307
[S:1]1[CH:5]=[C:4]([CH2:6][C:7]#[N:8])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.C1COCC1>[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH2:8])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Komponenten

5

Edukt 2

HCID 76681Benzo[b]thiophene-3-acetonitrileHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 26743Benzo[b]thiophene-3-ethanamineAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Reduce benzo[b]thiophen-3-yl-acetonitrile (350.9 mg, 2.0 mmol) in Et2O (6.0 mL) with 1.0 M LAH in THF (6.0 mL) at 0-10° C. for 1 hour. Carry out Fieser work-up to remove the LAH. Concentrate and pass through an SCX column washing with MeOH and then eluting with 2.0 M NH3 in MeOH. Concentrate the eluant and purify twice by chromatography, eluting with 75:20:5 EtOAc/hexanes/2.0 M NH3 in MeOH and then with 70:20:10 EtOAc/hexanes/2.0 M NH3 in MeOH to yield the title compound (86.5 mg, 24%): MS ES+ 178.2 (M+H)+, 161.2 (base peak); 1H NMR (DMSO-d6) δ 7.94 (d, J=7.3 Hz, 1H), 7.81 (d, J=7.8 Hz, 1H), 7.40-7.33 (m, 3H), 3.32 (br s, 2H), 2.88 (br s, 4H).

Aufarbeitung

  1. customCarry out Fieser work-up to remove the LAH
  2. concentrationConcentrate
  3. washpass through an SCX column washing with MeOH
  4. washeluting with 2.0 M NH3 in MeOH
  5. concentrationConcentrate the eluant
  6. custompurify twice by chromatography
  7. washeluting with 75:20:5 EtOAc/hexanes/2.0 M NH3 in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-b97631f153a04c69ba51a911544e7543
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560463B2

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