ORDER
REPRINTS
2908
LOCHER
93%) as slightly yellow oil, which crystallised upon triturating with ether
and cooling. Due to a presumably low melting point, the solid could
not be isolated at RT and was converted into the corresponding picrate.
Mp. (picrate) 126–129ꢀC (EtOH); dH 7.28 (d, 1H, 8 Hz), 7.05–6.99 (m, 3H),
6.50–6.46 (m, 2H), 3.82 (s, 6H, OCH3), 3.67 (s, 2H, NCH2), 3.63 (s, 2H,
ArCH2N), 2.83 (t, 2H, 4 Hz, NCH2CH2), 2.78 (t, 2H, 4 Hz, NCH2CH2); dC
160.3, 159.1, 137.0, 133.0, 131.5, 131.1, 130.1, 126.6, 126.3, 118.2, 104.1,
98.5, 55.4 and 55.2 and 55.1 (OCH3 and ArCH2N and NCH2), 50.1
(NCH2CH2), 28.3 (NCH2CH2); m/z (%) 317 (Mþ, 13), 179 (20), 166 (12),
152 (14), 151 (100), 121 (29), 91 (16), 77 (16); lmax (nm/dm3 molÀ1 cmÀ1) 280
(3110), 224 (9590); nmax (cmÀ1, Nujol) 1620, 1505, 1295, 1205, 1160, 1040,
940, 840, 800; Anal. calc. for C24H23ClN4O9: C 52.7; H 4.2; N 10.2; Found:
C 53.1, H 4.5, N 10.2%.
N-(20,40-Dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline6g.N-Benzo-
triazol-1-ylmethyl-1,2,3,4-tetrahydroisoquinoline 4g (0.50 g, 1.9 mmol),
anhydrous AlCl3 (1.00 g, 7.5 mmol) and 1,3-dimethoxybenzene (0.26 g,
1.9 mmol) were refluxed for 24 h in CHCl3. Product 6g (0.52 g, 96%) was
obtained as colourless oil, which crystallised upon contact with either at 4ꢀC.
Since the solid could not be isolated at RT, the corresponding picrate was
obtained. Mp. (picrate) 133–135ꢀC (EtOH); dH 7.31 (d, 1H, 9 Hz), 7.09
(d, 3H, 2 Hz), 7.01–6.98 (m, 1H), 6.15–6.45 (m, 2H), 3.81 (s, 6H, OCH3),
3.67 (s, 4H, ArCH2 and ArCH2N), 2.89 (t, 2H, 5 Hz, NCH2CH2), 2.77
(t, 2H, 4 Hz, NCH2CH2); dC 160.2, 159.1, 135.4, 134.6, 131.4, 128.8,
126.8, 126.1, 125.6, 118.8, 104.0, 98.5, 55.9 (OCH3), 55.4 (NCH2 and
ArCH2N), 50.4 (NCH2CH2), 29.0(NCH 2CH2); m/z (%) 283 (Mþ, 14),
207 (21), 151 (100), 145 (28), 132 (20), 121 (33), 91 (23), 77 (21); lmax
(nm/dm3 molÀ1 cmÀ1) 278 (600), 207 (4730); nmax (cmÀ1, Nujol) 1620,
1500, 1295, 1215, 1155, 1050, 745, 670; Anal. calc. for C24H24N4O9: C
56.3; H 4.7; N 10.9; Found: C 55.9, H 4.6, N 10.7%.
N-(20-Hydroxy-10-naphthylmethyl)-7-bromo-1,2,3,4-tetrahydroisoquino-
line 7a. The reaction between N-benzotriazol-1-ylmethyl-7-bromo-1,2,3,4-
tetrahydroisoquinoline 4a (0.70 g, 2.0 mmol), anhydrous AlCl3 (1.09 g,
8.2 mmol) and 2-hydroxynaphthalene (0.29 g, 2.0 mmol) yielded compound
7a (0.69 g, 93%) as creamy white crystals. Mp. 127–128ꢀC (EtOH);
dH 7.87–7.70(m, 3H), 7.47 (t, 1H, 6 Hz), 7.35–7.26 (m, 2H), 7.17–7.00(m,
3H), 4.33 (s, 2H, NCH2), 3.82 (s, 2H, ArCH2N), 2.94 (bs, 4H, NCH2CH2);
dC 156.7, 135.6, 132.8, 132.6, 130.5, 129.9, 129.6, 129.1, 128.7, 126.6, 122.7,
121.1, 119.7, 119.3, 110.7, 55.8 (NCH2), 54.9 (ArCH2N), 49.9 (NCH2CH2),
28.0(NCH CH2); lmax (nm/dm3 molÀ1 cmÀ1) 335 (1910), 290 (2790), 279
2
(3750), 230 (11770); nmax (cmÀ1, Nujol) 3400, 1625, 1315, 1270, 1245, 1225,
1160, 1100, 950, 895, 820, 750, 670; Anal. calc. for C20H18BrNO: C 65.2; H
4.9; N 3.8; Found: C 65.5, H 5.1, N 3.6%.