Ammonia → 10-(3-Chloropropyl)-10H-phenoxazine

Participants

Reaction Steps

To a suspension of sodium amide (1.72 g) in 100 ml of liquid ammonia, 7 g (0.038 mol) of phenoxazine was added. After stirring for 30 minutes, 6.3 g (0.04 mol., 3.96 mL) of 1-bromo-3-chloropropane was added slowly with constant stirring. After one more hour, ammonia was allowed to evaporate and solid ice pieces were added carefully followed by cold water. When the reaction ceased, the mixture was extracted three times with ether. The ether solution was washed three times with water, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on silica gel. Petroleum ether-ethylacetate (9 mL+3 mL) eluted the pure title compound (7.94 g) as white crystals. VU-λmax (MeOH) 218, 238 and 321 nm; IR (KBr) 3070, 2860, 1630, 1490, 1380, 1275, 920, 815 and 740 cm-1 ; 1H-NMR (δ) 6.47-6.82 (m, 8H, ArH, H1 -H4 and H6 -H9), 2.11 (m, 2H, H1), 3.63 (m, 2H, HK), and 3.69 (m, 2H, Hm); 13C-NMR (1H decoupled) 111.23 (C1 and C9), 115.50 (C4 and C6), 121.07 (C3 and C7), 123.70 (C2 and C8), 133.03 (C1' and C9'), 144.92 (C4' and C6'), 27.82 (C1), 41.09 (CK) and 42.63 (Cm); EIMS (m/z) 259 (M+).

Provenance & Evidence