ACCEPTED MANUSCRIPT
N-(4-Methylphenyl)morpholine (1).23 Pale brown solid (666 mg, 75%), mp 44–45 °C (from
hexane) (lit. 47.3–48 °C) 1Н NMR (DMSO-d6+CCl4 (1:2), 400 MHz, ppm): δ 7.00 (d, J=8.4 Hz,
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2H), 6.76 (d, J=8.4 Hz, 2H), 3.76 (t, J=4.8 Hz, 4H), 3.05 (t, J=4.8 Hz, 4H), 2.26 (s, 3H). C
NMR (DMSO-d6+CCl4 (1:2), 101 MHz, ppm): δ 148.6, 128.9, 127.8, 115.2, 65.9, 49.0, 19.9.
HR-MS (ESI+): calcd for C11H16NO [M+H]+: 178.1226; found 178.1226.
N-Phenylmorpholine (2).23 Pale brown solid (579 mg, 71%), mp 55–56 °C (from hexane)(lit.
52.5-53.4 °C). 1Н NMR (CDCl3, 400 MHz, ppm): δ 7.34–7.28 (m, 2H), 6.97–6.91 (m, 3H), 3.90
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(t, J=4.8 Hz, 4H), 3.19 (t, J=4.8 Hz, 4H). C NMR (CDCl3, 101 MHz, ppm): δ 151.3, 129.2,
120.1, 115.6, 66.9, 49.4. HR-MS (ESI+): calcd for C10H14NO [M+H]+: 164.1070; found
164.1072.
N-(4-Methoxyphenyl)morpholine (3).24 Pale brown solid (680 mg, 70%), mp 70–72 °C (from
1
hexane)(lit. 71-72 °C). Н NMR (DMSO-d6+CCl4 (1:2), 400 MHz, ppm): δ 6.82 (d, J=9.1 Hz,
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2H), 6.76 (d, J=9.1 Hz, 2H), 3.76 (t, J=4.8 Hz, 4H), 3.73 (s, 3H), 2.99 (t, J=4.8 Hz, 4H). C
NMR (DMSO-d6+CCl4 (1:2), 101 MHz, ppm): δ 153.1, 145.0, 116.9, 113.7, 66.0, 54.6, 50.0.
HR-MS (ESI+): calcd for C11H16NO2 [M+H]+: 194.1176; found 194.1186.
N-(4-methylphenyl)pyrrolidine (4).25 Brown solid (415 mg, 51%), mp 40–42 °C (from
1
hexane)(lit. 40-42 °C). Н NMR (DMSO-d6+CCl4 (1:2), 400 MHz, ppm): δ 6.92 (d, J=8.0 Hz,
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2H), 6.40 (d, J=8.0 Hz, 2H), 3.24 (t, J=6.4 Hz, 4H), 2.24 (s, 3H), 2.02 (t, J=6.4 Hz, 4H). C
NMR (DMSO-d6+CCl4 (1:2), 101 MHz, ppm): δ 145.3, 128.9, 123.1, 111.2, 47.1, 24.8, 19.8.
HR-MS (ESI+): calcd for C11H16N [M+H]+: 162.1277; found 162.1280.
N-(4-Methoxyphenyl)piperidine hydrochloride (5).26 Brown solid (958 mg, 84%), mp 185–
1
187 °C (from 85% EtOH) (lit. 186-187 °C). H NMR (400 MHz, CDCl3): δ 13.73 (br. s, 1H),
7.84 (d, J=8.9 Hz, 2H), 6.97 (d, J=8.9 Hz, 2H), 3.83 (s, 3H), 3.62 (d, J=11.4 Hz, 2H), 3.23 (dd,
J=22.3 Hz, 10.5 Hz, 2H), 2.72 (q, J=13.4 Hz, 2H), 2.02 (d, J=13.4 Hz, 1H), 1.92 (d, J=14.4 Hz,
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2H), 1.57–1.47 (m, 1H). C NMR (CDCl3, 101 MHz, ppm): δ 160.2, 135.6, 122.7, 115.2, 57.6,
55.7, 23.0, 21.7. HR-MS (ESI+): calcd for C12H18NO [M+H]+: 192.1383; found 192.1386.
N-Cyclohexyl-4-methylaniline (6).27 Brown solid (749 mg, 79%), mp 43–44 °C (from 85%
1
EtOH) (lit. 40-41 °C). Н NMR (CDCl3, 400 MHz, ppm): δ 6.99 (d, J=8.3 Hz, 1H), 6.56 (d,
J=8.3 Hz, 1H), 3.56 (br.s, 1H), 3.28–3.21 (m, 1H), 2.26 (s, 3H), 2.10–2.06 (m, 2H), 1.80–1.75
(m, 2H), 1.69–1.64 (m, 1H), 1.44–1.33 (m, 2H), 1.29–1.11 (m, 3H). 13C NMR (CDCl3, 101
MHz, ppm): δ 145.1, 129.8, 126.2, 113.5, 52.1, 33.6, 26.0, 25.1, 20.4. HR-MS (ESI+): calcd for
C13H20N [M+H]+: 190.1590; found 190.1592.
4-Methyl-(N-phenyl)piperidine hydrochloride (7). Pale brown solid (762mg, 72%), mp 155–
157 °C (from 85% EtOH). 1Н NMR (DMSO-d6+CCl4 (1:2), 400 MHz, ppm): δ 13.75 (br. s, 1H),
8.04 (m, 2H), 7.52–7.43 (m, 3H), 3.64 (m, 2H), 3.46–3.44 (m, 2H), 2.18 (m, 2H), 1.91–1.87 (m,
3H), 1.09 (d, J= 6.0 Hz, 3Н). 13C NMR (DMSO-d6, 101 MHz, ppm):δ 143.1, 129.2, 121.5, 95.5,
55.2, 30.4, 27.4, 20.8. HR-MS (ESI+): calcd for C12H18N [M+H]+: 176.1434; found 176.1437.
4-Ethoxy-N-((tetrahydrofuran-2-yl)methyl)aniline hydrochloride (8). Brown solid (929 mg,
1
72%), mp 98–100 °C (from 85% EtOH). Н NMR (DMSO-d6+CCl4 (1:2), 400 MHz, ppm): δ
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