Reaktion #414767

Reaktionsgleichung

phenoxyacetic acid

borane trimethylamine complex

2-(N-n-propylamino)-5-methoxytetralin

→

2-[N-n-propyl,N-2-(phenyloxy)ethyl-amino]-5-methoxytetralin

Lösungsmittel

—

xylenes

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   SonstigeThe cooled reaction mixture
3. 3
   Extraktionwas extracted with NaHCO3
4. 4
   Trocknenthe organic layer was dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   Sonstigeproduct was isolated
8. 8
   SonstigeThe free base thus isolated

Vorschrift

A mixture of 2-(N-n-propylamino)-5-methoxytetralin (7.0 g, 0 0319 mol; prepared according to J. Chem. Soc., 1965, pp. 26-36), phenoxyacetic acid (4.86 g, 0.0319 mol), and borane trimethylamine complex (2.33 g, 0.0319 mol) was refluxed in xylenes overnight. The cooled reaction mixture was extracted with NaHCO3 and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting oil was subjected to flash chromatography (silica; 9:1 pet ether/EtOAc) and product was isolated: NMR of the free base (300 MHz, CDCl3): δ 7.3-6.6(m, 8H), 4.0(t, 2H), 3.7(s, 3H), 3.1-2.5(m, 9H), 2.1(m, 1H), 1.7-1.4(m, 3H), 0.9(t, 3H). The free base thus isolated was converted to hydrochloride salt by the addition of dry ether-HCL.

Quelle