N-Methylhomoveratrylamine → 3,4-Dichloro-N-[4-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]butyl]-N-(1-methylethyl)benzenesulfonamide

HRID 2290955

Reaktionsgleichung

Reaktionsgleichung von HRID 2290955
[CH:1]([N:4]([CH2:16][CH2:17][CH2:18][CH:19]=O)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[CH3:21][NH:22][CH2:23][CH2:24][C:25]1[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[C:27]([O:28][CH3:29])[CH:26]=1>C(O)C.O=[Pt]=O>[Cl:15][C:10]1[CH:9]=[C:8]([S:5]([N:4]([CH2:16][CH2:17][CH2:18][CH2:19][N:22]([CH2:23][CH2:24][C:25]2[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[C:27]([O:28][CH3:29])[CH:26]=2)[CH3:21])[CH:1]([CH3:2])[CH3:3])(=[O:6])=[O:7])[CH:13]=[CH:12][C:11]=1[Cl:14]

Komponenten

5

Edukt 2

HCID 77039N-MethylhomoveratrylamineHCID 13770967N-isopropyl-N-(4-oxobutyl)-3,4-dichlorobenzenesulfonamide

Produkt 1

HCID 137709683,4-Dichloro-N-[4-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]butyl]-N-(1-methylethyl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

The aldehyde prepared in the preceding paragraph (8.90 g, 0.027 m) and N-methyl-homoveratrylamine (5.29 g, 0.027 m) in absolute ethanol (100 ml) containing PtO2 (0.6 g) was shaken under hydrogen (7 hours) and the reaction filtered and stripped to provide the crude product (13.32 g) as a dark greenish gum. This material was chromatographed, after removal of a small amount of insoluble solid, on dry column silica gel (500 g) with 30% methanol/70% ethyl acetate to provide the title compound (7.26 g) as a clear white gum.

Aufarbeitung

  1. filtrationthe reaction filtered
  2. customto provide the crude product (13.32 g) as a dark greenish gum
  3. customThis material was chromatographed
  4. customafter removal of a small amount of insoluble solid
  5. dry with materialon dry column silica gel (500 g) with 30% methanol/70% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fe203a9032f446659f56f459b8ba90a1
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04618711

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