Diethylamine → 10-(3'-Diethylaminopropyl)phenoxazine

Participants

Reaction Steps

1 g (4.31 mmol) of the product of Example 1 was dissolved in 150 mL of anhydrous acetonitrile, and 1.5 g KI, 2.13 g K2CO3 and 1.6 mL (15.4 mmol) of N,N-diethylamine were added. The mixture was refluxed overnight until a substantial amount of product was formed (TLC, System B, Rf =0.40). The reaction mixture was diluted with water and extracted with ether three times. The ether layer was washed with water and dried over anhydrous Na2SO4 and evaporated. The crude oil was subjected to column chromatography for purification. Ethylacetate-petroleum ether (50 mL+50 mL) eluted the title compound as the free base as a colorless oil, which was dried and used for NMR studies. An ethereal solution of the free base was treated with an excess of tartaric acid to separate the hygroscopic tartrate salt (1.2 g). UV-λmax (MeOH) 215, 238 and 320 nm; IR (CHCl3) 3378, 2974, 2838, 1453, 1375, 1155, 973 and 722 cm-1 ; 1H-NMR (`δ`) 6.51-6.80 (m, 8H, ArH, H1 -H4 and H6 -H9), 1.16 (t, 6H, Hc and Hd), 1.70 (m, 2H, H1), 2.50 (q, 4H, Ha and Hb, J=7 Hz), 3.42-3.63 (m, 4H, Hk and Hm); 13C-NMR 111.54 (C1 and C9), 115.49 (C4 and C6), 121.21 (C3 and C7), 123.85 (C2 and C8), 132.72 (C1' and C9'), 144.95 (C4' and C6'), 8.21 (Cc and Cd), 19.90 (C1), 40.72 (Ca and Cb), 45.87 (Cm), and 48.50 (Ck); EIMS (m/z) 296 (M+).

Provenance & Evidence