1,4-Dioxane hydrochloride → 4-[(1-Bromo-2-naphthalenyl) methoxy]piperidine hydrochloride

Beteiligte Stoffe

Reaktionsschritte

A solution of 15 (1.117 g, 2.65 mmole) in 4N HCl/dioxane (10 ml) was stirred at room temperature for 1 hr. The solvent was evaporated in vacuo to give a white precipitant which upon washing repeatedly with hexane gave 0.9 g of 1 (2.53 mmole) (95%). Anal (C16H19BrClNO) C,H,N. For chromatographic and spectral analysis, 0.7 g of 1 was dissolved in water (30 ml) and the solution was made basic with conc NH4OH. The resulting oily precipitate was extracted with CH2Cl2 (3×50 ml). The CH2Cl2 fraction was washed with saturated NaHCO3, H2O, brine and dried over anhydrous MgSO4. The dried CH2Cl2 solution was evaporated in vacuo to give 0.6 g of a light yellow oil that solidified upon standing as the free base form of 1. A single component was detected by TLC (hexane/ethyl acetate, 90:10) Rf, 0; (conc NH4OH/methanol/hexane/ethyl acetate, 1:1:3:6) Rf, 0.35; NMR (CDCl3) d 1.7-2.1 (m, 4H, CH2 -ring) d 2.8-3.2 (m, 4H, ring- (CH2)2 --NH), d 3.7 (m, 1H, O--CH-ring), d 4.8 (2H, 5, CH2 --O--) d7.4-8.3 (m, 5H, naphthyl).

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