2002
C.-Z. Dong et al. / Bioorg. Med. Chem. 13 (2005) 1989–2007
(s, 2H, CH2CN), 3.42 (q, 2H, J = 7.00, CH2CH3), 3.59
(m, 12H, OCH2), 3.78 (t, 2H, J = 4.83, CH2CH2OPh),
4.04 (t, 2H, J = 4.83, CH2OPh), 4.43 (s, 2H, NH2),
6.80 (d, 2H, J = 8.46, Har), 7.11 (d, 2H, J = 8.46, Har).
4.3.14. 2-Tetradecyloxyphenylacetamidoxime (11n).
Compound 11n was prepared according to the above
general procedure from 7n (2.00 g, 6.04 mmol), hydrox-
ylamine hydrochloride (2.20 g, 31.7 mmol), K2CO3
(4.60 g, 33.3 mmol) and isolated as beige crystals
4.3.10.
4-(8-(2-Ethoxyethoxy)octyloxy)phenylacet-
(1.32 g, 60% yield): mp 74–76 ꢁC; IR (KBr, cmꢀ1
)
1
amidoxime (11j). Compound 11j was prepared according
to the above general procedure from 7j (1.13 g,
3.30 mmol), hydroxylamine hydrochloride (1.20 g,
17.3 mmol), K2CO3 (2.60 g, 18.8 mmol) and isolated as
a pale yellow solid (0.84 g, 68% yield): mp 55–57 ꢁC;
1H NMR (CDCl3): d 1.14 (t, 3H, J = 7.00, CH3), 1.27
(m, 8H, (CH2)ch), 1.52 (dt, 2H, J = 6.43, CH2CH2O),
1.69 (dt, 2H, J = 6.81, CH2CH2OPh), 3.33 (s, 2H,
CH2C@N), 3.39 (t, 2H, J = 6.71, CH2O), 3.46 (q, 2H,
J = 7.00, CH2CH3), 3.51 (s, 4H, OCH2CH2O), 3.84 (t,
2H, J = 6.44, CH2OPh), 4.45 (s, 2H, NH2), 6.76 (d,
2H, J = 8.47, Har), 7.10 (d, 2H, J = 8.47, Har), 8.10 (br
s, 1H, OH).
3456, 3361 (NH2), 3235 (OH, large), 1666 (C@N); H
NMR (CDCl3): d 0.80 (t, 3H, J = 6.36, CH3), 1.18
(m, 22H, (CH2)11CH3), 1.73 (dt, 2H, J = 6.79,
CH2CH2O), 3.40 (s, 2H, CH2CN), 3.92 (t, 2H,
J = 6.44, CH2OPh), 4.80 (s, 2H, NH2), 6.79 (m, 2H,
Har), 7.13 (m, 2H, Har).
4.3.15.
4-n-Heptyloxy-3-(2-n-hexyl-1,3-dioxolan-2-yl)-
phenylacetamidoxime (11o). Compound 11o was pre-
pared according to the above general procedure from
crude 7o (1.66 mmol), hydroxylamine hydrochloride
(0.60 g, 8.63 mmol), K2CO3 (1.30 g, 9.42 mmol) and iso-
1
lated as a pale yellow oil (0.34 g, 49% yield): H NMR
(CDCl3): d 0.80 (m, 6H, CH3), 1.20 (m, 16H, (CH2)ch
4.3.11. 4-(14-(Tetrahydropyran-2-yloxy)tetradecyloxy)-
phenylacetamidoxime (11k). Compound 11k was pre-
pared according to the above general procedure from
7k (2.80 g, 6.52 mmol), hydroxylamine hydrochloride
(2.30 g, 33.0 mmol), K2CO3 (5.00 g, 36.2 mmol) and iso-
lated as a pale yellow solid (1.71 g, 57% yield). An ana-
lytical sample was obtained by recrystallization (CH2Cl2
and
CH2CH2CO2),
1.75
(dt,
2H,
J = 6.96,
CH2CH2OPh), 2.07 (m, 2H, CH2CO2), 3.35 (s, 2H,
CH2C@N), 3.77 (m, 2H, CH2OPh), 3.92 (m, 4H, OCH2-
CH2O), 4.44 (s, 2H, NH2), 6.77 (d, 1H, J = 8.32, Har),
7.00 (br s, 1H, OH), 7.20 (dd, 1H, J = 2.26, 8.32, Har),
7.29 (d, 1H, J = 2.26, Har).
1
and petroleum ether): mp 89–90 ꢁC; H NMR (CDCl3):
4.3.16.
3-n-Heptyl-4-n-heptyloxyphenylacetamidoxime
d 1.20 (m, 18H, (CH2)ch), 1.52 (m, 6H, CH2CH2-
CH2OPh and OCH2CH2), 1.70 (m, 6H, OCHCH2 and
CH2CH2OPh), 3.33 (s, 2H, CH2C@N), 3.46 (m, 2H,
(CH2O)ch), 3.66 (m, 2H, (CH2O)cycle), 3.85 (t, 2H,
J = 6.49, CH2OPh), 4.43 (s, 2H, NH2), 4.51 (t, 1H,
J = 2.92, OCHO), 6.77 (d, 2H, J = 8.61, Har), 7.11 (d,
2H, J = 8.61, Har).
(11p). Compound 11p was prepared according to the
above general procedure from 7p (0.29 g, 0.88 mmol),
hydroxylamine hydrochloride (0.33 g, 4.75 mmol),
K2CO3 (0.70 g, 5.07 mmol) and isolated as a pale yellow
solid (0.19 g, 59% yield). An analytical sample (white
crystals) was obtained by recrystallization (abs EtOH):
1
mp 78–79 ꢁC; H NMR (CDCl3): d 0.82 (m, 6H, CH3),
1.24 (m, 18H, (CH2)ch), 1.72 (dt, 2H, J = 6.81,
CH2CH2OPh), 2.50 (t, 2H, J = 7.65, CH2Ph), 3.32 (s,
2H, CH2C@N), 3.86 (t, 2H, J = 6.28, CH2OPh), 4.43
(s, 2H, NH2), 6.69 (d, 1H, J = 8.94, Har), 6.96 (m, 2H,
Har).
4.3.12.
2-(4-Tetradecyloxyphenyl)propionamidoxime
(11l). Compound 11l was prepared according to the
above general procedure from 7l (0.41 g, 1.2 mmol),
hydroxylamine hydrochloride (0.43 g, 6.2 mmol),
K2CO3 (0.91 g, 6.6 mmol) and isolated as a white solid
(203 mg, 45.2% yield): mp 85–87 ꢁC; IR (KBr, cmꢀ1
)
4.3.17. 4-(N,N-Di-n-heptylamino)phenylacetamidoxime
(11q). Compound 11q was prepared according to the
above general procedure from 7q (1.00 g, 3.04 mmol),
hydroxylamine hydrochloride (1.06 g, 15.2 mmol),
K2CO3 (2.31 g, 16.7 mmol) and isolated as a red oil
(0.88 g, 80% yield): IR (Nujol, cmꢀ1) 3506, 3400
1
3490, 3375 (NH2), 3180 (OH, large), 1655 (C@N); H
NMR (CDCl3): d 0.81 (t, 3H, J = 6.50, CH2CH3), 1.19
(m, 25H, (CH2O)ch and CHCH3), 1.70 (dt, 2H,
J = 6.65, CH2CH2OPh), 3.49 (q, 1H, J = 6.75, CHCH3),
3.86 (t, 2H, J = 6.20, CH2OPh), 4.30 (br s, 2H, NH2),
4.90 (br s, 1H, OH), 6.79 (d, 2H, J = 8.10, Har), 7.14
(d, 2H, J = 8.10, Har).
1
(NH2), 3225 (OH), 1665 (C@N); H NMR (CDCl3): d
0.81 (t, 6H, J = 6.35, CH3), 1.23 (m, 16H, (CH2)ch),
1.48 (m, 4H, NCH2CH2), 3.13 (t, 4H, J = 7,36,
NCH2), 3.28 (s, 2H, CH2C@N), 4.41 (s, 2H, NH2),
5.22 (br s, 1H, OH), 6.51 (d, 2H, J = 8.69, Har), 7.00
(d, 2H, J = 8.59, Har).
4.3.13.
2-Methyl-2-(4-tetradecyloxyphenyl)propion-
amidoxime (11m). Compound 11m was prepared accord-
ing to the above general procedure from 7m (0.50 g,
1.4 mmol), hydroxylamine hydrochloride (0.50 g,
7.2 mmol), K2CO3 (1.06 g, 7.7 mmol) and isolated as a
white solid (0.48 g, 87% yield): mp 63–65 ꢁC; IR (KBr,
cmꢀ1) 3490, 3375 (NH2), 3180 (OH, large), 1655
(C@N); 1H NMR (CDCl3): d 0.81 (t, 3H, J = 6.41,
CH2CH3), 1.20 (m, 22H, (CH2O)ch), 1.46 (s, 6H,
C(CH3)2), 1.70 (dt, 2H, J = 7.07, CH2CH2OPh), 3.87
(t, 2H, J = 6.50, CH2OPh), 4.23 (br s, 2H, NH2), 6.79
(d, 2H, J = 8.82, Har), 7.22 (d, 2H, J = 8.82, Har), 8.44
(br s, 1H, OH).
4.3.18.
4-(N,N-Di-n-octylamino)phenylacetamidoxime
(11r). Compound 11r was prepared according to the
above general procedure from 7r (1.00 g, 2.80 mmol),
hydroxylamine hydrochloride (0.97 g, 14.0 mmol),
K2CO3 (2.13 g, 15.4 mmol) and isolated as a brown oil
(0.71 g, 65% yield): IR (Nujol, cmꢀ1) 3495, 3376
1
(NH2), 3180 (OH), 1664 (C@N); H NMR (CDCl3): d
0.81 (t, 6H, J = 6.72, CH3), 1.22 (m, 20H, (CH2)ch),
1.48 (m, 4H, NCH2CH2), 2.88 (t, 4H, J = 7.25,