Methanol → Sertraline

HRID 1393710

Reaktionsgleichung

Reaktionsgleichung von HRID 1393710
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[N:19][CH3:20])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CO.[H][H]>[Ni].ClC1C=CC=CC=1>[CH3:20][NH:19][C@@H:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:10][CH2:11]1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 9796475N-(4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene)methanamineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 68617SertralineAusbeute 0,86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)naphthalenylidene]methanamine (Ketimine) (50 g), methanol (300 ml), Raney Nickel (0.15 g wet basis) and chlorobenzene (25 ml) are charged into a reaction vessel. The mixture is hydrogenated at 5 to 6 kg/cm2 over pressure of hydrogen for 6 to 7 hrs at about 28 to 30° C. The catalyst is removed by filtration and the cake is washed with 50 ml methanol. The cis to trans ratio is 87-89/9-13. The amount of dehalogenated by product is <0.1%. Sertraline racemate free base thus formed is treated with hydrochloric acid (24 ml, 33%) and predominantly isomer of sertraline HCl racemate is filtered [Cis>98%, trans<2%, dehalogenation product<0.1%, yield 0.86 to 0.88%].

Aufarbeitung

  1. customThe catalyst is removed by filtration
  2. washthe cake is washed with 50 ml methanol

Quellen und Nachweise

ORD-Eintrag
ord-bbf3cdd8ae9b4a6092673f4ae80371ff
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345201B2

Verknüpfte Notizen

Wird geladen…