SYNTHESIS AND SOME TRANSFORMATIONS
1155
equimolar amount of NaBH4 with stirring and cooling
with ice water; the reaction temperature did not exceed
20°C. Then the reaction mixture was stirred at room
temperature for another 1 h. After distilling off
methanol, the residue was alkalinized with 20%
aqueous NaOH, extracted with ether, dried, and
evaporated. The residue was distilled.
(6H, CHCHMe2, J 6.8), 0.87 d (6H, CH2CH2CHMe2, J
6.5), 1.30 d (6H, OCHMe2, J 6.0), 0.87–1.65 m (13H,
3.5-CH2, CH2CH2CHMe2, CH2CH2N, OCHCH), 2.43 t
(2H, CH2CH2N , J 8.0), 3.08 d.d.d (1H, OCH, J 11.5,
6.1, 1.5), 3.47–3.59 m and 3.61–3.72 m (2H, OCH2),
3.63 s (2H, NCH2C6H4), 4.50 septet (1H, OCHMe2, J
6.0), 6.73 m and 7.14 m (4H, C6H4). Found, %: C
77.26; H 11.30; N 3.76. C25H43NO2. Calculated, %: C
77.07; H 11.12; N 3.59.
Benzyl-{2-[2-isopropyl-4-(3-methylbutyl)tetra-
hydropyran-4-yl]ethyl}amine (V). Yield 70%; bp
170–175°C (1 mmHg). IR spectrum, ν, cm–1: 3310
(3,4-Dimethoxybenzyl)-{2-[2-isopropyl-4-(3-me-
thylbutyl)tetrahydropyran-4-yl]ethyl}amine (IX).
Yield 65% (mixture of two diastereoisomers, 80:20),
bp 193–195°C (1 mmHg). IR spectrum, ν, cm–1: 3310
1
(NH); 1600, 1580 (C=C, Ar). Н NMR spectrum (300
MHz), δ, ppm (J, Hz): 0.84 d and 0.87 d (6H,
CHCHMe2, J 6.7), 0.87 d (6H, CH2CHMe2, J 6.6),
0.88–1.66 m (13H, 3.5-CH2,CH2CH2CHMe2, CHCHMe2,
NH), 2.45 t (2H, CH2CH2N, J 8.0), 3.09 d.d.d (1H, OCH,
J 11.4, 6.1, 1.5), 3.47–3.59 m (1Н, ОСН2), 3.66–3.72
m (1H, OCH2), 3.72 s (2H, CH2Ph), 7.13–7.30 m (5H,
C6H5). Found, %: C 79.84; H 11.18; N 4.33.
C22H37NO. Calculated, %: C 79.70; H 11.25; N 4.22.
1
(NH); 1605, 1590 (C=C, Ar). Н NMR spectrum (300
MHz), δ, ppm (J, Hz): 0.84 d and 0.86 d (6H,
ОCHCHMe2, J 6.8), 0.87 d (6H, CH2CH2CHMe2, J
6.6), 0.90–1.65 m (13H, 3,5-CH2, CH2CH2CHMe2,
CH2CH2NH, OCHCH), 2.44 t (2H, CH2CH2 N, J 8.0),
3.09 d.d.d (1H, OCH, J 11.4, 6.0, 1.5), 3.49–3.72 m
(2H, OCH2), 3.63 s (2H, NCH2Ar), 3.77 s and 3.80 s
(3H and 3H, OCH3), 6.71–6.77 m and 6.85–6.87 m
(3H, C6H3). Found, %: C 73.50; H 10.69; N 3.73.
C24H41NO3. Calculated, %: C 73.61; H 10.55; N 3.58.
{2-[2-Isopropyl-4-(3-methylbutyl)tetrahydropyran-
4-yl]ethyl}-(4-methoxybenzyl)amine (VI). Yield 71%,
bp 195–200°C (2.5 mmHg). IR spectrum, ν, cm–1:
1
3320 (NH); 1610, 1590 (C=C, Ar). Н NMR spectrum
(300 MHz), δ, ppm (J, Hz): 0.84 d and 0.87 d (6H,
CHCHMe2, J 6.8), 0.87 d (6H, CH2CHMe2, J 6.6),
0.88–1.65 m (13H, 3,5-CH2,CH2CH2CHMe2, OCHCH,
NHCH2CH2), 2.43 t (2H, CH2CH2N, J 8.0), 3.08 d.d.d
(1H, OCH, J 11.4, 5.9, 1.5), 3.47–3.72 m (2H, OCH2),
3.64 s (2H, CH2C6H4), 3.76 s (3H, OCH3), 6.77 m and
7.17 m (4H, C6H4). Found, %: C 76.60; H 11.00; N
4.04. C23H39NO2. Calculated, %: C 76.40; H 10.87; N 3.87.
(4-Ethoxy-3-methoxybenzyl)-{2-[2-isopropyl-4-
(3-methylbutyl)tetrahydropyran-4-yl]ethyl}amine
(X). Yield 64% (mixture of two diastereoisomers,
65 : 35), bp 210–215°C (2 mmHg). IR spectrum, ν,
1
cm–1: 3305 (NH); 1600, 1560 (C=C, Ar). Н NMR
spectrum (300 MHz), δ, ppm (J, Hz): 0.84 d and 0.84 d
(6H, CH2CH2CHMe2, J 6.8), 0.87 d (6H, CHCHMe2, J
6.6), 0.88–1.16 m (4H, 3,5-CH2), 1.40 t (3H, CH2CH3,
J 7.0), 1.26–1.73 m (9H, CH2CH2CH, CH2CH2NH,
OCHCH), 2.44 t and 2.55 t (2H, CH2CH2N, J 8.1 and
7.2), 3.06–3.13 m (1H, OCH), 3.62 s and 3.63 s (2H,
NCH2Ar), 3.47–3.72 m (2H, OCH2), 3.80 s (3H,
OCH3), 3.98 q (2H, OCH2CH3, J 7.0), 6.72–6.86 m
(3H, C6H3). Found, %: C 74.29; H 10.52; N 3.32.
C25H43NO3. Calculated, %: C 74.03; H 10.69; N 3.45.
[4-({2-[2-Isopropyl-4-(3-methylbutyl)tetrahydro-
pyran-4-yl]ethylamino}methyl)phenyl]dimethyl-
amine (VII). Yield 67%, bp 200–205°C (1.5 mmHg).
IR spectrum, ν, cm–1: 3306 (NH); 1605, 1582 (C=C,
1
Ar). Н NMR spectrum (300 MHz), δ, ppm (J, Hz):
0.84 d and 0.87 d (6H, CHCHMe2, J 6.8), 0.87 d (6H,
CH2CHMe2, J 6.6), 1.02–1.18 m (4H, 3,5-CH2), 1.25–
1.68 m (9H, CH2CH2CHMe2, OCHCH, NHCH2CH2),
2.43 t (2H, CH2CH2N, J 8.0), 2.91 s (6H, NMe2), 3.08
d.d.d (1H, OCH, J 11.6, 6.1, 1.5), 3.60 s (2H, NCH2C6H4),
3.52–3.69 m (2H, OCH2), 6.60 m and 7.08 m (2H and
2H, C6H4). Found, %: C 76.77; H 11.11; N 7.30.
C24H42N2O. Calculated, %: C 76.95; H 11.30; N 7.48.
Furan-2-yl-methyl-{2-[2-isopropyl-4-(3-methyl-
butyl)tetrahydropyran-4-yl]ethyl}amine (XI). Yield
70%, bp 170–175°C (3 mmHg). IR spectrum, ν, cm–1:
1
3330 (NH), 1675, 1605 (C=C, furan). Н NMR spec-
trum (300 MHz), δ, ppm (J, Hz): 0.84 d and 0.87 d
(6H, CHCHMe2, J 6.7), 0.88 d (6H, CH2CHMe2, J
6.7), 0.83–0.97 m and 1.12–1.62 m (12H, CH, CH2),
1.10 br.s (1H, NH), 2.43 t (2H, CH2CH2N, J 8.1), 3.08
d.d.d (1H, OCH, J 11.3, 5.9, 2.0), 3.48–3.71 m (2H,
OCH2), 3.68 s (2H, CH2-furyl), 6.11 d and 6.26 d. d
(2H, OCH=CH, OCH=CH-furyl, J 3.2, 2.0), 7.32 d
(4-Isopropoxybenzyl)-{2-[2-isopropyl-4-(3-me-
thylbutyl)tetrahydropyran-4-yl]ethyl}amine (VIII).
Yield 68%, bp 185–190°C (1.5 mmHg). IR spectrum,
1
ν, cm–1: 3300 (NH); 1600, 1580 (C=C, Ar). Н NMR
spectrum (300 MHz), δ, ppm (J, Hz): 0.84 d and 0.86 d
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 6 2014