Methanol → (S)-(+)-N-methyl-3-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine

HRID 1686175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1686175
[CH3:1][N:2]([CH2:5][CH2:6][CH:7]([O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)OC.[CH3:24]O>[Ni]>[CH3:1][NH:2][CH2:5][CH2:6][C@:7]([CH3:24])([O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 46913234N-methyl-N-methoxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine

Produkt 1

HCID 42598152(S)-(+)-N-methyl-3-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 935NickelKatalysator

Versuchsvorschrift

N-methyl-N-methoxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine obtained in example 3 was dissolved in 15 mL of methanol with 0.67 g of Raney-nickel were charged in a glass autoclave. The resulting solution was hydrogenated at 50□ for 12 hours. Upon completion of hydrogenation the reaction mixture was filtered and solvent is removed under reduced pressure, and then the desired compound is obtained as an oily compound (12.0 g, 96.4% by HPLC assay). 1H NMR (400 MHz, CDCl3) δ (ppm)=2.2 (m, 1H), 2.4 (m, 1H), 2.4 (s, 3H), 2.8 (m, 2H), 5.8 (m, 1H), 6.8 (d, 1H), 6.9 (m, 1H), 7.1 (d, 1H), 7.2 (d, 1H), 7.3 (d, 1H), 7.4 (m, 1H), 7.5 (m, 2H), 7.8 (m, 1H), 8.3 (m, 1H).

Aufarbeitung

  1. additionwere charged in a glass autoclave
  2. filtrationUpon completion of hydrogenation the reaction mixture was filtered
  3. customsolvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a9e6e6fee484852bec3064b5b6db641
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148549B2

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