Hydrochloric Acid → 5-Methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1059716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059716
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2.Cl>CCO.[Pt]=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 137542835-Methoxyisoquinoline

Produkt 1

HCID 139482495-Methoxy-1,2,3,4-tetrahydroisoquinolineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of the product of step (a) (6.11 g, 384 mmol) in EtOH (200 ml) was added platinum oxide (0.611 g) followed by concentrated HCl (3.2 ml, 38.4 mmol). The reaction mixture was hydrogenated at 345 kPa (50 p.s.i.) at room temperature for 4 h after which time the catalyst was filtered off and washed with EtOH. The filtrate was evaporated under reduced pressure to afford the subtitle compound as a colourless solid (7.27 g, 95%). 1H NMR (D6-DMSO) δ: 2.80 (2H, m), 3.35 (2H, m), 3.80 (3H, s), 4.20 (2H, s), 6.80 (1H, d), 6.90 (1H, d), 7.20 (1H, t), 9.45 (2H, bs).

Aufarbeitung

  1. filtrationafter which time the catalyst was filtered off
  2. washwashed with EtOH
  3. customThe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cd8497618ee6480fbf3ce7b25dadc4b7
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521629B2

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