Synthesis of N-Acylalkylenediamines
2923
the completion of reaction (TLC), the solvent was removed, the residue was
extracted with n-hexane (3 ꢀ 5 mL) and washed with water (10 mL) and aq.
sodium bicarbonate (10%, 10 mL).The crude product was further purified
by column chromatography (pet.ether : ethyl acetate ¼ 8 : 2).
N-(2,3-Dihydrobenzo[1,4]dioxin-2-carbonyl)piperazine (6k). M.p. ¼ 84–
2
1 1
8
58C; IR (KBr): 1640, 3450 cm ; H NMR (300 MHz, CDCl ): d 2.15 (s, 1H,
3
NH), 2.80–2.90 (m, 2H), 2.95–3.00 (m, 2H), 3.50–3.65 (m, 2H), 3.70–3.80
(
m, 2H), 4.40 (dd, J ¼ 12.0, 8.5 Hz, 1H), 4.50 (dd, J ¼ 12.0, 2.5 Hz, 1H), 4.90
13
(
dd, J ¼ 8.5, 2.5 Hz, 1H), 6.90–7.10 (m, 4H); C NMR (75 MHz, CDCl ):
3
d ¼ 40.2 (2C), 45.7, 50.3, 65.1, 70.5, 115.1, 120.2, 122.4, 123.9, 144.2, 145.6,
þ
1
70.2; EIMS : m/z (%) ¼ 248 (M , 25), 111 (100); Anal. calcd. for
C H ,N O : C, 62.89; H, 6.50; N, 11.28. Found: C, 63.02; H, 6.41; N, 11.35.
2 3
13
16
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(
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