JAFAROV et al.
1278
CH3, J = 7.5 Hz), 1.21–1.32 m (8H, CH2), 1.65 m (2H,
CH2), 2.49 d.d and 2.62 d.d (1H each, CH2S, J = 14.0,
7.7 Hz), 3.03 q (4H, CH2N), 3.62 m (2H, CH2O),
4.04 m (1H, CHO), 4.59 s (2H, OCH2N), 7.15–7.34 m
(5H, C6H5). 13C NMR spectrum, δC, ppm: 14.4, 15.2,
16.4, 18.2, 20.2, 35.4, 37.5, 39.6, 69.5, 88.4, 91.5.
Mass spectrum, m/z (Irel, %): 340 (9) [M + H]+, 339
(11) [M]+, 313 (10) [M – OH]+, 306 (69) [M – OH –
CH2]+, 265 (100) [M – C3H7S]+, 182 (15) [M –
C9H20NO]+, 112 (21) [C7H15N]+, 82 (33). Found, %:
C 67.02; H 9.74; N 4.10; S 9.39. C19H33NO2S. Cal-
culated, %: C 67.21; H 9.38; N 4.14; S 9.44.
[M + H]+, 395 (9) [M]+, 378 (70) [M – OH]+, 364 (70)
[M – OH – CH2]+, 324 (100) [M – C3H9S]+, 322 (10)
[M – C4H10CH3]+, 203 (13) [C11H23SO]+, 112 (80)
[C7H15]+, 82 (33). Found, %: C 69.61; H 10.41;
N 3.51; S 8.03. C23H41NO2S. Calculated, %: C 69.82;
H 10.45; N 3.54; S 8.10.
1-{[1-Phenoxy-3-(propylsulfanyl)propan-2-yl-
oxy]methyl}piperidine (15) was synthesized from
6.78 g (0.03 mol) of 3, 0.9 g (0.03 mol) of paraformal-
dehyde, and 2.55 g (0.03 mol) of piperidine (8). Yield
6.97 g (72%), bp 190–192°C (1 mm Hg), nD20 = 1.5294,
d240 = 1.0456; MRD = 95.46, calcd. 95.37. IR spectrum,
ν, cm–1: 3050 (C–Harom), 2895 (CH3), 2850 (CH2),
1585 (C=Carom), 1250 (C–N), 1050 (C–O), 650 (C–S).
1H NMR spectrum, δ, ppm: 1.01 t (3H, CH3, J =
7.3 Hz), 1.21 m (2H, CH2), 1.32 m (6H, CH2), 2.49 d.d
and 2.61 d.d (1H each, CH2S, J = 14.0, 7.7 Hz), 3.01 q
(4H, CH2N), 3.62 m (2H, OCH2), 4.04 m (1H, OCH),
4.51 s (2H, OCH2N), 7.15–7.34 m (5H, C6H5).
13C NMR spectrum, δC, ppm: 14.4, 15.2, 17.5, 20.45,
26.21, 35.4, 36.4, 39.6, 69.9, 86.4, 88.5. Mass spec-
trum, m/z (Irel, %): 324 (10) [M + H]+, 323 (20) [M]+,
248 (17) [M – C3H7S]+, 240 (10) [M – C5H9N]+,
230 (8) [M – C3H7S – H2O]+, 212 (25) [M – C7H7O –
H2O]+, 202 (100) [M – C7H7NO]+, 147 (25),
[C10H11O]+, 75 (60) [C3H7S]+. Found, %: C 66.92;
H 8.96; N 4.28; S 9.80. C18H29NO2S. Calculated, %:
C 66.83; H 9.04; N 4.33; S 9.91.
N-Butyl-N-{[1-phenoxy-3-(propylsulfanyl)pro-
pan-2-yloxy]methyl}butan-1-amine (13) was synthe-
sized from 6.78 g (0.03 mol) of 3, 0.9 g (0.03 mol) of
paraformaldehyde, and 3.87 g (0.03 mol) of dibutyl-
amine (6). Yield 8.47 g (77%), bp 198–199 (1 mm Hg),
nD20 = 1.5140, d420 = 1.0788; MRD 111.21, calcd. 111.36.
IR spectrum, ν, cm–1: 3060 (C–Harom), 2910 (CH3),
2850 (CH2), 1585 (C=Carom), 1200 (C–N), 1050 (C–O),
1
735 (C–S). H NMR spectrum, δ, ppm: 0.98 t (6H,
CH3, J = 7.1 Hz), 1.01 t (3H, CH3, J = 7.1 Hz), 1.21–
1.32 m (10H, CH2), 1.45–1.51 m (2H, CH2), 1.65 m
(2H, CH2), 2.49 d.d and 2.61 d.d (1H each, CH2S, J =
14.0, 7.7 Hz), 3.03 q (4H, CH2N), 3.62 m (2H, CH2O),
4.04 m (1H, CHO), 4.59 s (2H, OCH2N), 7.15–7.34 m
(5H, C6H5). 13C NMR spectrum, δC, ppm: 14.4, 15.2,
16.4, 18.2, 20.2, 35.4, 38.6, 69.9, 86.4, 88.5. Mass
spectrum, m/z (Irel, %): 368 (9) [M + H]+, 367 (8) [M]+,
278 (12) [M – C4H9S]+, 209 (15) [M – C9H20NO]+, 203
(13) [C11H23SO]+, 176 (100) [M – C10H23SO]+,
82 (33). Found, %: C 68.57; H 10.25; N 3.72;
S 8.65. C21H37NO2S. Calculated, %: C 68.62; H 10.15;
N 3.81; S 8.72.
4-{[1-Phenoxy-3-(propylsulfanyl)propan-2-yl-
oxy]methyl}morpholine (16) was synthesized from
6.78 g (0.03 mol) of 3, 0.9 g (0.03 mol) of paraformal-
dehyde, and 2.61 g (0.03 mol) of morpholine (9). Yield
7.21 g (74%), bp 192–194°C (1 mm Hg), nD20 = 1.5312,
d240 = 1.0889; MRD = 92.50, calcd. 92.48. IR spectrum,
ν, cm–1: 3060 (C–Harom), 2900 (CH3), 2840 (CH2),
1600, 1500 (C=Carom), 1250 (C–N), 1100 (C–O), 750
N-Pentyl-N-{[1-phenoxy-3-(propylsulfanyl)pro-
pan-2-yloxy]methyl}pentan-1-amine (14) was syn-
thesized from 6.78 g (0.03 mol) of 3, 0.9 g (0.03 mol)
of paraformaldehyde, and 4.71 g (0.03 mol) of di-
pentylamine (7). Yield 7.84 g (71%), bp 203–204°C
(1 mm Hg), nD20 = 1.5012, d420 = 0.9692; MRD = 120.31,
calcd. 120.61. IR spectrum, ν, cm–1: 3060 (C–Harom),
2910 (CH3), 2845 (CH2), 1585 (C=Carom), 1200 (C–N),
1
(C–S). H NMR spectrum, δ, ppm: 1.01 t (3H, CH3,
J = 7.1 Hz), 1.21–1.32 m (4H, CH2), 1.45 m (2H,
CH2), 2.49 d.d and 2.61 d.d (1H each, CH2S, J = 14.0,
7. 7 Hz), 3. 03 q (4H, CH2N), 3. 75 m (4H,
NCH2CH2O), 3.82 m (2H, OCH2), 4.04 m (1H, CHO),
4.51 s (2H, OCH2N), 7.13–7.36 m (5H, C6H5).
13C NMR spectrum, δC, ppm: 14.4, 15.2, 17.5, 19.2,
20.45, 26.21, 35.4, 36.4, 39.6, 69.6, 69.9, 86.4, 88.15.
Mass spectrum, m/z (Irel, %): 325 (10) [M]+, 255 (5)
[M – C4H8N]+, 232 (7) [M – C3H7S – H2O]+, 226 (8)
[M – C5H9NO]+, 208 (9) [M – C5H9ON – H2O]+, 204
(100) [M – C7H7NO]+, 147 (26) [M – C7H7NO]+, 101
(25), 75 (54) [C3H7S]+. Found, %: C 62.52; H 8.27;
N 4.26; S 9.74. C17H27NO3S. Calculated, %: C 62.73;
H 8.36; N 4.30; S 9.85.
1
1050 (C–O), 750 (C–S). H NMR spectrum, δ, ppm:
0.95 t (6H, CH3, J = 7.4 Hz), 1.01 t (3H, CH3, J =
7.5 Hz ), 1.21–1.32 m (12H, CH2), 1.45 m (2H, CH2),
1.65 m (2H, CH2), 2.49 d.d and 2.61 m (1H each,
CH2S, J = 14.0, 7.7 Hz), 3.03 q (4H, CH2N), 3.62 m
(2H, CH2O), 4.04 m (1H, CHO), 4.59 s (2H, OCH2N),
7.14–7.35 m (5H, C6H5). 13C NMR spectrum, δC, ppm:
14.4, 15.2, 16.5, 18.2, 20.2, 24.3, 35.4, 38.6, 69.9,
86.4, 88.6. Mass spectrum, m/z (Irel, %): 396 (15)
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 9 2019