[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([NH2:16])[CH2:8][CH2:9][CH:10]2[CH2:15][CH2:14]O[CH2:12][CH2:11]2)[CH:2]=1.C(O)C.C([O-])([O-])=O.[K+].[K+].[Na+].[Cl-:27]>Br>[ClH:27].[ClH:27].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:8][CH2:9][CH:10]3[CH2:15][CH2:14][N:16]2[CH2:12][CH2:11]3)[CH:2]=1A solution of 1-(3-pyridyl)-3-(4-oxanyl)propylamine (1.00 g, 4.54 mmol) in 48% aqueous HBr (15 mL) was saturated with HBr gas. The mixture was heated in a pressure tube at 100°–120° C. for 12 h. The tube was cooled in ice water and the contents transferred to a 250 mL round bottom flask. Removal of the volatiles by rotary evaporation afforded a light yellow solid. Absolute ethanol (200 mL) and solid K2CO3 (10 g) were added and the mixture was heated at reflux for 8 h. The mixture was filtered through a Celite plug, which was then washed with ethanol (25 mL). The combined filtrates were concentrated by rotary evaporation; the solid obtained was suspended in saturated aqueous NaCl (10 mL) and extracted with chloroform (4×30 mL). The combined organic extracts were dried (K2CO3), filtered and concentrated by rotary evaporation to give a dark brown oil. Short path distillation (120°–122° C., 2 mm) provided 0.750 g of the desired free base as a colorless oil (81.7% yield).
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