compound 12a afforded the product as a colourless oil;
νmax(CDCl3)/cmϪ1 3061, 3027, 2930, 2857, 1599, 1495, 1454,
1360, 1177, 1098, 1020, 961, 930, 816, 748, 700, 664, 575 and
556; δH (CDCl3, 300 MHz) 7.78 (d, J 9.0, 2 H), 7.33 (d, J 6.0, 2
H), 7.29–7.25 (m, 2 H), 7.19–7.14 (m, 3 H), 4.01 (t, J 6.0, 2 H),
2.57 (t, J 8.0, 2 H), 2.44 (s, 3 H), 1.65–1.52 (m, 4 H) and 1.39–
1.21 (m, 6 H); δC(CDCl3, 75.46 MHz) 144.47, 142.43, 132.99,
129.62, 128.15, 128.03, 127.62, 125.41, 70.45, 35.64, 31.09,
28.77, 28.54, 25.04 and 21.37; m/z (EI) 346 (M+), 174, 117, 104
and 91 [Found (HRMS): m/z 346.1595. Calc. for C20H26SO3:
346.1603].
158.34, 150.48, 147.42, 141.73, 128.68, 128.20, 128.06, 125.74,
123.43, 122.65, 120.17, 115.90, 49.13, 35.39, 33.97, 31.10, 28.53,
24.63, 22.90 and 22.66; m/z (ESI) 331 [M + H]+ {Found
(HRMS): m/z 331.2164. Calc. [M + H]+ for C23H26N2:
331.2174}.
(5-Phenylpentyl)(1,2,3,4-tetrahydroacridin-9-yl)amine 2b
A similar procedure to that described for the preparation of the
preceding compound afforded the product as a yellow oil;
νmax(CDCl3)/cmϪ1 3347, 3061, 3025, 2932, 2857, 1615, 1603,
1562, 1497, 1452, 1420, 1358, 1298, 1125, 939, 909, 762 and 700;
δH (CDCl3, 300 MHz) 7.91 (t, J 9.0, 2 H), 7.59–7.50 (m, 1 H),
7.36–7.25 (m, 3 H), 7.20–7.14 (m, 3 H), 3.90 (s, 1 H), 3.54–3.42
(m, 2 H), 3.10–2.98 (m, 2 H), 2.69–2.59 (m, 4 H), 1.93–1.90 (m,
4 H), 1.71–1.61 (m, 4 H) and 1.47–1.39 (m, 2 H); δC(CDCl3,
75.46 (MHz) 158.17, 150.32, 147.34, 141.92, 128.57, 128.06,
128.01, 127.87, 125.46, 123.23, 122.59, 120.00, 115.60, 49.06,
35.45, 33.89, 31.30, 30.78, 26.16, 24.48, 22.79 and 22.54; m/z
(ESI) 345 [M + H]+ {Found (HRMS): m/z 345.2326. Calc.
[M + H]+ for C24H28N2: 345.2330}.
8-Phenyloctyl toluene-4-sulfonate 12e
A similar procedure to that described for the preparation of
compound 12a afforded the product as a colourless oil;
νmax(CDCl3)/cmϪ1 3061, 3027, 2926, 2855, 1923, 1807, 1655,
1599, 1495, 1454, 1358, 1306, 1292, 1177, 1098, 1030, 941, 814,
748, 700 and 664; δH (CDCl3, 300 MHz) 7.79 (d, J 9.0, 2 H), 7.33
(d, J 6.0, 2 H), 7.27–7.25 (m, 2 H), 7.19–7.15 (m, 3 H), 4.01 (t, J
6.0, 2 H), 2.58 (t, J 8.0, 2 H), 2.44 (s, 3 H), 1.64–1.55 (m, 4 H)
and 1.35–1.20 (m, 8 H); δC(CDCl3, 75.46 MHz) 144.47, 142.55,
133.01, 129.64, 128.18, 128.04, 127.66, 125.41, 70.50, 35.73,
31.23, 29.04, 28.91, 28.60, 25.10 and 21.41; m/z (EI) 360 (M+),
188, 117, 104 and 91 [Found (HRMS): m/z 360.1753. Calc. for
C21H28SO3: 360.1759].
(6-Phenylhexyl)(1,2,3,4-tetrahydroacridin-9-yl)amine 2c
A similar procedure to that described for the preparation of
compound 12a afforded the product as a yellow oil; νmax(CDCl3)/
cmϪ1 3345, 3061, 3025, 2930, 2857, 1615, 1582, 1562, 1497,
1454, 1420, 1360, 1298, 1125, 941, 909, 762 and 698; δH (CDCl3,
300 MHz) 7.92 (dd, J 9.0, 15.0, 2 H), 7.60–7.50 (m, 1 H), 7.36–
7.25 (m, 3 H), 7.20–7.15 (m, 3 H), 3.92 (s, 1 H), 3.49–3.45 (m, 2
H), 3.11–3.01 (m, 2 H), 2.77–2.65 (m, 2 H), 2.60 (t, J 8.0, 2 H),
1.96–1.90 (m, 4 H), 1.67–1.58 (m, 4 H) and 1.48–1.35 (m, 4 H);
δC(CDCl3, 75.46 MHz) 158.33, 150.51, 147.47, 142.35, 128.71,
128.20, 128.11, 128.04, 125.52, 123.38, 122.69, 120.14, 115.74,
49.32, 35.66, 34.01, 31.55, 31.16, 28.81, 26.67, 24.66, 22.94 and
22.69; m/z (ESI) 359 [M + H]+ {Found (HRMS): m/z 359.2485.
Calc. [M + H]+ for C25H30N2: 359.2487}.
9-Phenylnonyl toluene-4-sulfonate 12f
A similar procedure to that described for the preparation of
compound 12a afforded the product as a colourless oil;
νmax(CDCl3)/cmϪ1 3063, 3027, 2928, 2855, 1599, 1495, 1454,
1360, 1177, 953, 916, 816, 748, 700, 664, 577 and 556; δH (CDCl3,
300 MHz) 7.79 (d, J 9.0, 2 H), 7.34 (d, J 9.0, 2 H), 7.30–7.25 (m,
2 H), 7.19–7.16 (m, 3 H), 4.01 (t, J 6.0, 2 H), 2.59 (t, J 8.0, 2 H),
2.44 (s, 3 H), 1.65–1.57 (m, 4 H) and 1.35–1.17 (m, 10 H);
δC(CDCl3, 75.46 MHz) 144.49, 142.68, 133.08, 129.68, 128.23,
128.09, 127.71, 125.44, 70.56, 35.81, 31.34, 29.15, 29.09, 28.75,
28.64, 25.16 and 21.47; m/z (EI) 374 (M+), 202, 117, 104 and 91
[Found (HRMS): m/z 374.1899. Calc. for C22H30SO3: 374.1916].
(7-Phenylheptyl)(1,2,3,4-tetrahydroacridin-9-yl)amine 2d
A similar procedure to that described for the preparation of
compound 2a afforded the product as a yellow oil; νmax(CDCl3)/
cmϪ1 3347, 3061, 3025, 2930, 2855, 1615, 1603, 1562, 1497,
1454, 1420, 1360, 1123, 1028, 943, 762 and 698; δH (CDCl3, 300
MHz) 7.92 (dd, J 9.0, 15.0, 2 H), 7.54 (t, J 8.0, 1 H), 7.36–7.19
(m, 3 H), 7.17–715 (m, 3 H), 3.92 (s, 1 H), 3.49–3.46 (m, 2 H),
3.11–2.99 (m, 2 H), 2.78–2.66 (m, 2 H), 2.59 (t, J 8.0, 2 H), 1.94–
1.90 (m, 4 H), 1.67–1.58 (m, 4 H) and 1.41–1.33 (m, 6 H);
δC(CDCl3, 75.46 MHz) 158.33, 150.54, 147.50, 142.51, 128.73,
128.21, 128.09, 125.47, 123.35, 122.71, 120.14, 115.71, 49.35,
35.75, 34.03, 31.62, 31.21, 29.09, 28.98, 26.72, 24.65, 22.95 and
22.70; m/z (ESI) 373 [M + H]+ {Found (HRMS): m/z 373.2643.
Calc. [M + H]+ for C26H32N2: 373.2644}.
10-Phenyldecyl toluene-4-sulfonate 12g
A similar procedure to that described for the preparation of
compound 12a afforded the product as a colourless oil;
νmax(CDCl3)/cmϪ1 3061, 3027, 2926, 2855, 1921, 1805, 1653,
1599, 1495, 1454, 1360, 1306, 1292, 1177, 1098, 1020, 959, 928
and 816; δH (CDCl3, 300 MHz) 7.79 (d, J 9.0, 2 H), 3.34 (d, J 9.0,
2 H), 7.30–7.25 (m, 2 H), 7.18–7.16 (m, 3 H), 4.01 (t, J 6.0, 2 H),
2.59 (t, J 8.0, 2 H), 2.44 (s, 3 H), 1.65–1.57 (m, 4 H) and 1.28–
1.21 (m, 12 H); δC(CDCl3, 75.46 MHz) 144.53, 142.79, 133.20,
129.71, 128.31, 128.14, 127.79, 125.47, 70.62, 35.89, 31.41,
29.33, 29.26, 29.20, 28.81, 28.73, 25.24 and 21.53; m/z (EI) 388
(M+), 216, 117, 104 and 91 [Found (HRMS): m/z 388.2060.
Calc. for C23H32SO3: 388.2072].
(8-Phenyloctyl)(1,2,3,4-tetrahydroacridin-9-yl)amine 2e
A similar procedure to that described for the preparation of
(4-Phenylbutyl)(1,2,3,4-tetrahydroacridin-9-yl)amine 2a
compound 12a afforded the product as a yellow oil;
A solution of THA (458 mg, 2.3 mmol) in THF (5 ml) was
added to a suspension of NaNH2 (180 mg, 4.6 mmol) in THF
(2 ml) under N2. The mixture was vigorously stirred at room
temperature for 45 min after which a solution of compound 12a
(700 mg, 2.3 mmol) in THF (14 ml) was added to it. The result-
ing orange–red mixture was stirred at room temperature for 24
h and then extracted with EtOAc. The extract was washed with
saturated aqueous Na2CO3 and work-up followed by flash
chromatography on NH3-saturated silica gel eluting with 30%
EtOAc in hexane afforded the product as a yellow oil (509 mg,
67%); νmax(CDCl3)/cmϪ1 3351, 3061, 3025, 2934, 2859, 1655,
1615, 1582, 1562, 1497, 1452, 1420, 1362, 1333, 1142, 943, 856,
762 and 700; δH (CDCl3, 300 MHz) 7.91 (t, J 9.0, 2 H), 7.55–7.52
(m, 1 H), 7.36–7.26 (m, 3 H), 7.21–7.14 (m, 3 H), 3.89 (s, 1 H),
3.49 (t, J 8.0, 2 H), 3.11–2.99 (m, 2 H), 2.70–2.56 (m, 4 H), 1.96–
1.87 (m, 4 H) and 1.77–1.67 (m, 4 H); δC(CDCl3, 75.46 MHz)
νmax(CDCl3)/cmϪ1 3354, 3061, 3025, 2928, 2855, 1615, 1582,
1562, 1497, 1454, 1420, 1358, 1296, 1273, 1121, 1028, 943, 909,
760 and 698; δH (CDCl3, 300 MHz) 7.92 (dd, J 9.0, 15, 2 H),
7.60–7.50 (m, 1 H), 7.36–7.24 (m, 3 H), 7.19–7.15 (m, 3 H), 3.92
(s, 1 H), 3.49–3.42 (m, 2 H), 3.06–3.04 (m, 2 H), 2.78–2.66 (m, 2
H), 2.59 (t, J 9.0, 2 H), 1.94–1.87 (m, 4 H), 1.67–1.58 (m, 4 H)
and 1.40–1.31 (m, 8 H); δC(CDCl3, 75.46 MHz) 158.46, 150.68,
147.56, 142.73, 128.79, 128.32, 128.17, 125.53, 123.47, 122.80,
120.23, 115.83, 49.50, 35.89, 34.10, 31.74, 31.38, 29.32, 29.23,
29.12, 26.87, 24.75, 23.04 and 22.79; m/z (ESI) 387 [M + H]+
{Found (HRMS): m/z 387.2789. Calc. [M + H]+ for C27H34N2:
387.2800}.
(9-Phenylnonyl)(1,2,3,4-tetrahydroacridin-9-yl)amine 2f
A similar procedure to that described for the preparation of
compound 2a afforded the product as a yellow oil; νmax(CDCl3)/
J. Chem. Soc., Perkin Trans. 1, 1997
175