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2.71 (dd, 1H, J¼12.9, 5.9 Hz, CHCH2N), 2.91 (dd, 1H, J¼13.2, 7.5 Hz,
CHCH2N), 3.46 (d, 1H, J¼13.2 Hz, NCH2Ar), 3.52 (d, 1H, J¼13.2 Hz,
NCH2Ar), 3.77 (s, 3H, OMe), 3.83 (s, 3H, OMe), 3.93 (br s, 2H,
2ꢂCH(CH3)2), 5.94 (dd, 1H, J¼7.3, 5.9 Hz, CHOCO), 6.74–6.72 (m, 3H,
4.4.7. 2-(N-3,4-Dimethoxyphenethyl-N-methylamino)-1-
phenylethyl N0,N0-diisopropylcarbamate (7c)
Yield 77%. Oil. IR (Golden-Gate): 2938, 1684 (C]O), 1515, 1438,
1261, 1137, 1047, 1029, 734, 699 cmꢁ1. 1H NMR (CDCl3)
d 1.20–1.24
ArH), 7.26–7.32 (m, 5H, ArH). 13C NMR (CDCl3)
d
21.5, 42.7, 46.3,
(m, 12H, 2ꢂCH–(CH3)2), 2.37 (s, 3H, NCH3), 2.64–2.66 (m, 4H,
NCH2CH2), 2.72 (dd, 1H, J¼13.3, 5.4 Hz, OCHCH2), 2.94 (dd, 1H,
J¼13.3, 7.6 Hz, OCHCH2), 3.83 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 3.94
(br s, 2H, 2ꢂCH(CH3)2), 5.89 (dd, 1H, J¼7.6, 5.4 Hz, OCH), 6.67–6.70
(m, 2H, ArH), 6.76 (d, 1H, J¼8.7 Hz, ArH), 7.22–7.35 (m, 5H, ArH). 13C
56.0, 56.1, 62.4, 62.9, 74.2,110.8,112.1,121.1,127.0,127.8,128.4, 132.1,
140.9, 148.1, 149.0, 155.1. MS (EI): m/z (%) 248 (7), 247 (45), 150
(100). Anal. Calcd for C25H36N2O4: C, 70.06; H, 8.47; N, 6.54. Found:
C, 70.13; H, 8.56; N, 6.51.
NMR (75 MHz, CDCl3)
d 21.3, 33.9, 42.9, 46.1, 56.1, 56.2, 60.2, 63.5,
74.3, 111.8, 112.6, 120.8, 126.9, 127.7, 128.5, 133.5, 141.0, 147.6, 149.2,
155.0. MS (EI): m/z (%) 443 (Mþþ1, 1), 297 (31), 291 (76), 248 (54),
208 (C12H18NO2, 100), 165 (84), 146 (63), 128 (25), 104 (47), 86 (57),
57 (47), 43 (72). Anal. Calcd for C26H38N2O4: C, 70.56; H, 8.65; N,
6.33. Found: C, 70.33; H, 8.78; N, 6.31.
4.4.3. 2-(N-(3,4-Dimethoxybenzyl)-N-methylamino)-1-(4-
methoxyphenyl)ethyl N0,N0-diisopropylcarbamate (6d)
Yield 68%. Oil. IR (KBr film): 1687 (C]O), 1514, 1250 (C–O) cmꢁ1
.
1H NMR (CDCl3)
d
1.16–1.25 (m, 12H, 2ꢂCH(CH3)2), 2.25 (s, 3H,
NMe), 2.68 (dd, 1H, J¼12.7, 6.2 Hz, CHCH2N), 2.86 (dd, 1H, J¼13.0,
7.3 Hz, CHCH2N), 3.43 (d, 1H, J¼13.2 Hz, NCH2Ar), 3.51 (d, 1H,
J¼12.7 Hz, NCH2Ar), 3.76 (s, 3H, OMe), 3.77 (s, 3H, OMe), 3.83 (s, 3H,
OMe), 3.86 (br s, 2H, 2ꢂCH(CH3)2), 5.80 (t, 1H, J¼6.6 Hz, CHOCO),
6.72 (br s, 3H, ArH), 6.83 (d, 2H, J¼8.8 Hz, ArH), 7.24 (d, 2H,
4.4.8. 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-4-
phenylisoquinoline (1c)
Yield 89%. Mp 79–81 ꢀC. IR (KBr film): 1514, 1265 cmꢁ1. 1H NMR
J¼8.8 Hz, ArH). 13C NMR (CDCl3)
d
21.5, 42.7, 46.1, 55.4, 55.9, 56.0,
(CDCl3)
d
2.42 (s, 3H, NMe), 2.54 (dd, 1H, J¼11.4, 8.8 Hz, CHCH2N),
3.02 (ddd, 1H, J¼11.4, 5.7, 1.3 Hz, CHCH2N), 3.58 (d, 1H, J¼14.5 Hz,
NCH2Ar), 3.63 (s, 3H, OMe), 3.68 (d, 1H, J¼14.5 Hz, NCH2Ar), 3.85 (s,
3H, OMe), 4.22 (t, 1H, J¼6.8 Hz, CH2CHPh), 6.34 (s, 1H, ArH), 6.56 (s,
62.4, 62.6, 73.8, 110.8, 112.1, 113.8, 121.1, 132.1, 133.0, 148.1, 149.0,
155.0, 159.2. MS (EI): m/z (%) 459 (Mþþ1, 5), 314 (30), 197 (37), 151
(100). Anal. Calcd for C26H38N2O5: C, 68.10; H, 8.35; N, 6.11. Found:
C, 68.34; H, 8.36; N, 6.24.
1H, ArH), 7.17–7.30 (m, 5H, ArH). 13C NMR (CDCl3)
d 45.6, 46.0, 56.0,
56.1, 58.2, 62.1, 109.0, 112.2, 126.7, 127.4, 128.6, 130.0, 130.1, 137.8,
144.8. MS (EI): m/z (%) 284 (Mþþ1, 10), 283 (Mþ, 62), 282 (21), 240
(87), 209 (100). Anal. Calcd for C18H21NO2: C, 76.29; H, 7.47; N, 4.94.
Found: C, 76.43; H, 7.55; N, 5.02.
4.4.4. 2-(N-(3-(Benzyloxy)-4-methoxybenzyl)-N-methylamino)-1-
(4-(benzyloxy)phenyl)ethyl N0,N0-diisopropylcarbamate (6e)
Yield 51%. Oil. IR (KBr film): 1686 (C]O), 1512, 1260 (C–O) cmꢁ1
.
1H NMR (CDCl3)
d
1.19–1.29 (m, 12H, 2ꢂCH(CH3)2), 2.23 (s, 3H,
NMe), 2.71 (dd, 1H, J¼13.2, 6.2 Hz, CHCH2N), 2.89 (dd, 1H, J¼12.7,
7.5 Hz, CHCH2N), 3.44 (d, 1H, J¼13.2 Hz, NCH2Ar), 3.52 (d, 1H,
J¼12.7 Hz, NCH2Ar), 3.86 (s, 3H, OMe), 3.88 (br s, 2H, 2ꢂCH(CH3)2),
5.01 (s, 2H, OCH2Ph), 5.04 (s, 2H, OCH2Ph), 5.90 (t, 1H, J¼6.6 Hz,
CHOCO), 6.78–6.98 (m, 5H, ArH), 7.25–7.47 (m, 12H, ArH). 13C NMR
4.4.9. 2,3,4,5-Tetrahydro-3-methyl-1-phenyl-1H-3-benzo-
azepine (2a)60
Yield 97%. Mp 73–75 ꢀC. IR (KBr film): 2940, 1679, 1486, 1438,
1131, 754, 700 cmꢁ1. 1H NMR (CDCl3)
d 2.41–2.44 (m, 1H, CH2), 2.43
(s, 3H, NMe), 2.87–2.96 (m, 3H, CH2), 3.11–3.23 (m, 2H, CH2), 4.40
(d,1H, J¼8.8 Hz, CHPh), 6.70 (d,1H, J¼7.5 Hz, ArH), 7.15–7.41 (m, 8H,
(CDCl3) d 21.6, 22.0, 42.6, 46.4, 56.3, 62.2, 62.6, 70.2, 71.1, 73.7, 111.7,
ArH). 13C NMR (CDCl3)
d 36.7, 47.9, 50.1, 57.4, 63.2, 126.47, 126.59,
114.8,127.7,127.8,128.2, 128.5, 128.7, 128.8, 128.9, 133.2,137.3,148.1,
148.3, 148.9, 155.2, 158.6. MS (EI): m/z (%) 270 (23), 228 (30), 227
(100). Anal. Calcd for C38H46N2O5: C, 74.72; H, 7.59; N, 4.59. Found:
C, 74.89; H, 7.56; N, 4.71.
126.62, 128.4, 128.7, 128.8, 129.7, 141.6, 143.4, 144.6. MS (EI): m/z (%)
238 (Mþþ1, 34), 237 (Mþ, 21), 180 (C14H1þ2, 100), 147 (C10H13Nþ, 62),
133 (C9H11Nþ, 84), 115 (72). Anal. Calcd for C17H19N: C, 86.03; H,
8.07; N, 5.90. Found: C, 86.35; H, 7.99; N, 5.82.
4.4.5. 2-(N-Methyl-N-phenylethylamino)-1-phenylethyl N0,N0-
diisopropylcarbamate (7a)
4.4.10. 2,3,4,5-Tetrahydro-1-(4-methoxyphenyl)-3-methyl-1H-3-
benzoazepine (2b)
Yield 71%. Oil. IR (KBr film): 1686 (C]O), 1287 (C–O), 1047,
698 cmꢁ1. 1H NMR (CDCl3)
d
1.21–1.25 (m, 12H, 2ꢂCH(CH3)2), 2.40
Yield 88%. Mp 78–80 ꢀC. IR (KBr film): 2933, 1502, 1363, 1148,
(s, 3H, NMe), 2.69–2.77 (m, 5H, CH2NCH2CH2), 2.96 (dd, 1H, J¼13.4,
868, 518 cmꢁ1 1H NMR (CDCl3)
. d 2.40 (s, 3H, NMe), 2.48 (m, 1H,
7.7 Hz, CHCH2N), 3.95 (br s, 2H, 2ꢂCH(CH3)2), 5.90 (dd, 1H, J¼7.9,
CH2), 2.78–2.88 (m, 2H, CH2), 2.98–3.10 (m, 3H, CH2), 3.16 (s, 3H,
OCH3), 4.35 (t, 1H, J¼4.6 Hz, CH2CHPh), 6.69 (d, 1H, J¼7.5 Hz, ArH),
5.3 Hz, CHOCO), 7.14–7.36 (m, 10H, ArH). 13C NMR (CDCl3)
d 21.3,
34.2, 42.8, 46.2, 60.1, 63.5, 74.2, 126.1, 126.9, 127.8, 128.6, 129.0,
140.7, 140.9, 155.0. MS (EI): m/z (%) 291 (MþꢁPhCH2, 27), 148
(MþꢁPhCHOCb, 100), 105 (PhCH2CHþ2 , 35). Anal. Calcd for
C24H34N2O2: C, 75.35; H, 8.96; N, 7.32. Found: C, 74.98; H, 8.96; N,
7.55.
7.07–7.28 (m, 7H, ArH). 13C NMR (CDCl3)
d 36.5, 37.6, 48.0, 49.7, 57.4,
62.6, 122.2, 126.6, 127.0, 128.6, 130.0, 130.2, 141.5, 142.7, 143.6, 147.8.
MS (EI): m/z (%) 252 (MþꢁCH3, 89), 165 (77), 146 (88), 115 (98), 57
(100). Anal. Calcd for C18H21NO: C, 80.86; H, 7.92; N, 5.24. Found: C,
80.99; H, 7.98; N, 5.22.
4.4.6. 1-(4-Methoxyphenyl)-2-(N-methyl-N-phenylethyl-
amino)ethyl N0,N0-diisopropylcarbamate (7b)
4.4.11. 2,3,4,5-Tetrahydro-7,8-dimethoxy-3-methyl-1-phenyl-1H-3-
benzoazepine (2c)61
Yield 65%. Oil. IR (KBr film): 2973, 2933, 1685 (C]O), 1510, 1260,
1044, 733, 701 cmꢁ1
.
1H NMR (CDCl3)
d
1.18–1.27 (m, 12H,
Yield 90%. Mp 80–81 ꢀC (lit.62 103–105 ꢀC). IR (Golden-Gate):
2ꢂCH(CH3)2), 2.37 (s, 3H, NMe), 2.68–2.74 (m, 5H, CH2NCH2CH2),
2.93 (dd, 1H, J¼12.8, 7.5 Hz, CHCH2N), 3.80 (s, 3H, OMe), 3.90 (br s,
2H, 2ꢂCH(CH3)2), 5.84 (t, 1H, J¼6.6 Hz, CHOCO), 6.86–6.88 (m, 2H,
2938, 1513, 1448, 1271, 1216, 1098, 1013, 732, 701 cmꢁ1 1H NMR
.
(CDCl3) d 2.40–2.47 (m, 4H, NCH3, CH2), 2.75–3.11 (m, 5H, CH2, CH2),
3.61 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 4.30 (d, 1H, J¼7.8 Hz, OCH),
ArH), 7.14–7.29 (m, 7H, ArH). 13C NMR (CDCl3)
d
21.4, 34.2, 42.9,
6.26 (s, 1H, ArH), 6.68 (s, 1H, ArH), 6.92–7.58 (m, 5H, ArH). 13C NMR
46.0, 55.4, 60.2, 63.3, 73.9, 114.0, 126.1, 128.3, 128.5, 129.0, 133.1,
140.8, 155.2, 159.3. MS (EI): m/z (%)148 (MþꢁOCH3PhCHOCb, 100),
105 (PhCH2CHþ2 , 51). Anal. Calcd for C25H36N2O3: C, 72.78; H, 8.80;
N, 6.79. Found: C, 72.87; H, 8.88; N, 6.64.
(CDCl3) d 36.1, 47.9, 49.8, 56.1, 56.3, 57.6, 63.2, 113.4, 113.9, 126.6,
128.6, 128.7, 133.8, 136.7, 143.5, 147.1, 147.2. MS (EI): m/z (%) 298
(Mþþ1, 1), 297 (Mþ, 91), 282 (25), 253 (18), 241 (60), 240 (78), 223
(23), 206 (100), 193 (63), 178 (29), 165 (36), 57 (17), 42 (21). Anal.