N-benzyl-4-phenylbutan-2-amine → HCID 12952408, Verbindung

HRID 1390911

Reaktionsgleichung

Reaktionsgleichung von HRID 1390911
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([Cl:15])=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:10]=1)=[O:4].[CH3:16][CH:17]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(=O)CC>[Cl:15][C:8]1[CH:7]=[CH:6][C:5]([CH:3]([OH:4])[CH2:2][N:26]([CH:17]([CH3:16])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:10][C:9]=1[S:11]([NH2:14])(=[O:13])=[O:12]

Komponenten

4

Edukt 2

HCID 4362644N-benzyl-4-phenylbutan-2-amineHCID 12952390Bromo-4'-chloro-3'-sulfamoylacetophenone

Produkt 1

HCID 12952408HCID 12952408, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 5-(2-bromoacetyl)-2-chlorobenzenesulphonamide (3.13 g) in butanone (50 ml) and N-(1-methyl-3-phenylpropyl)-N-(phenylmethyl)amine (4.8 g) was heated under reflux for 30 minutes. The solvent was removed under reduced pressure and the residue triturated with dry ether and filtered. The ether solution was evaporated to dryness and the product dissolved in ethanol (50 ml) and treated with sodium borohydride (0.3 g). The mixture was stirred for 30 minutes and a further aliquot of sodium borohydride (0.3 g) was added. The reaction mixture was acidified with 2N hydrochloric acid and the ethanol removed under reduced pressure. The concentrate was bastified with 5N sodium hydroxide and the mixture extracted with ethyl acetate (2 × 50 ml). The extracts were washed with water (2 × 50 ml), dried (MgSO4) and evaporated to dryness to give the product as a yellow oil, 4.6 g. This oil was purified by chromatography on preparative chromatographic plates (silica, CHCl3 /5% MeOH) and converted into a hydrochloride salt m.p. 120-125°.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customThe solvent was removed under reduced pressure
  4. customthe residue triturated with dry ether
  5. filtrationfiltered
  6. customThe ether solution was evaporated to dryness
  7. dissolutionthe product dissolved in ethanol (50 ml)
  8. additiontreated with sodium borohydride (0.3 g)
  9. additiona further aliquot of sodium borohydride (0.3 g) was added
  10. customthe ethanol removed under reduced pressure
  11. extractionthe mixture extracted with ethyl acetate (2 × 50 ml)
  12. washThe extracts were washed with water (2 × 50 ml)
  13. dry with materialdried (MgSO4)
  14. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-be5d3299eb8b48be9c1304ce65ab8405
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04140713

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