Efficient synthesis of 2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone hydrochloride

Abstract

The title compound (5) was prepared by a reaction sequence starting from 2,3,4,5-tetramethoxytoluene (1) via the Blanc reaction, oxidation and alkylation. The described method provides a good yield of the C-6 heterocyclic-substituted benzoquinone derivative and is suitable for the synthesis of other benzoquinone derivatives.

A convenient synthesis of 1,4-benzoquinones

“…Compound 3c , 13 red oil, 65% yield . 1 H NMR (400 MHz, CDCl 3 ): δ 3.96 (s, 3H, OC H 3 ), 3.94 (s, 3H, OC H 3 ), 3.65 (t, J = 4.0 Hz, 4H), 3.38 (s, 2H, C H 2 ), 2.44 (t, J = 4.0 Hz, 4H), 2.16 (s, 3H, C H 3 ); MS (ESI): m/z = 282 [M + H] + .…”

“…Compound 3b, 4 red oil, 82% yield. 1 H NMR (500 MHz, CDCl 3 ): δ 4.39 (s, 2H, CH 2 Br), 3.97 (s, 3H, OCH 3 ), 3.96 (s, 3H, OCH 3 ), 2.09 (s, 3H, CH 3 ); MS (ESI): m/z = 275 [M + H] + .Compound 3c,13 red oil, 65% yield.1 H NMR (400 MHz, CDCl 3 ): δ 3.96 (s, 3H, OCH 3 ), 3.94 (s, 3H, OCH 3 ), 3.65 (t, J = 4.0 Hz, 4H), 3.38 (s, 2H, CH 2 ), 2.44 (t, J = 4.0 Hz, 4H), 2.16 (s, 3H, CH 3 ); MS (ESI): m/z = 282 [M + H] + . Compound 3d, 2 red oil, 70% yield.…”

Practical synthesis of 2-(4-benzyl-piperazin-1-ylmethyl)-5, 6-dimethoxy-3-methyl-[1, 4]benzoquinone hydrochloride

“…benzoquinone 7 were prepared by the literature method[4][5][6][7][13][14][15][16][17][18][19][20][21].…”