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    Int. J. Mol. Sci.

    2017, 18, 2332 10 of 18

    3.2.5. N-(4-octylphenyl)-1-(2-hydroxyethyl)pyrrolidine-2-carboxamide (2d)


    Compound 2d was obtained following the procedure described for 2a, starting from 1d and
    2-bromoethanol. Yield: 73%; oil. 1 H-NMR δ = 9.62 (s, 1H, -NH), 7.53 (d, J = 8.1 Hz, 2H),
    7.10 (d, J = 8.1 Hz, 2H), 3.80–3.75 (m, 1H), 3.71–3.70 (m, 1H), 3.32–3.30 (m, 1H), 3.23–3.20 (m, 1H),
    2.88 (m, 1H), 2.74–2.71 (m, 1H), 2.55 (t, J = 7.3 Hz, 2H), 2.47–2.41 (m, 1H), 2.24–2.22 (m, 1H), 2.03–2.00
    (m, 1H), 1.82–1.80 (m, 2H), 1.49–1.52 (m, 2H), 1.26 (bs, 10H), 0.86 (t, J = 7.0 Hz, 3H); 13 C-NMR δ = 173.04,
    138.81, 135.90, 128.99, 119.52, 68.29, 61.13, 57.95, 54.38, 35.60, 32.10, 31.81, 30.87, 29.69, 29.49, 29.45,
    24.63, 22.88, 14.32. ESI-MS calculated: 332.48; Found: 333.4 [M + H]+ . Anal. (C21 H34 N2 O2 ), C, H, N.

    3.2.6. 1-(2-hydroxyethyl)-N-(naphthalen-1-yl)pyrrolidine-2-carboxamide (2e)


    Compound 2e was obtained following the procedure described for 2a, starting from 1e and
    2-bromoethanol. Yield: 66%; oil. 1 H-NMR δ = 10.23 (s, 1H, –NH), 8.23 (d, J = 7.3 Hz, 1H),
    8.01 (d, J = 7.7 Hz, 1H), 7.86 (d, 7.7 Hz, 1H), 7.65 (d, J = 8.1 Hz, 1H), 7.53–7.45 (m, 3H), 3.87–3.77
    (m, 2H), 3.45–3.44 (m, 1H), 3.39 (dd, J = 13.9, 4.0 Hz, 1H), 3.05–3.00 (m, 1H), 2.82–2.77 (m, 1H), 2.56–2.50
    (m, 1H), 2.36–2.26 (m, 1H), 2.13–2.10 (m, 1H), 1.93–1.90 (m, 2H); 13 C-NMR δ = 173.65, 134.30, 132.90,
    128.90, 126.54, 126.29, 126.16, 126.04,124.95, 120.91, 118.56, 68.90, 61.29, 58.26, 54.62, 31.09, 24.87. ESI-MS
    calculated: 284.15; Found: 285.3 [M + H]+ . Anal. (C17 H20 N2 O2 ), C, H, N.

    3.2.7. N-(biphenyl-2-yl)-1-(2-hydroxyethyl)pyrrolidine-2-carboxamide (2f)


    Compound 2f was obtained following the procedure described for 2a, starting from 1f and
    2-bromoethanol. Yield: 72%; oil. 1 H-NMR δ = 9.67 (s, 1H,–NH), 8.45 (d, J = 8.1 Hz, 1H),
    7.50 (d, J = 7.3 Hz, 2H), 7.45–7.24 (m, 5H), 7.18 (t, J = 6.9 Hz, 1H), 3.28–3.25 (m, 3H),
    3.19 (d, J = 9.9 Hz, 1H), 2.97–2.93 (m, 2H), 2.68–2.65 (m, 1H), 2.48–2.45 (m, 1H), 2.31–2.29 (m, 1H),
    2.16–2.14 (m, 1H), 2.09–2.00 (m, 1H), 1.65–1.63 (m, 1H); 13 C-NMR δ = 173.14, 139.08, 135.17, 132.25,
    130.17, 129.80, 128.98, 128.80, 127.95, 124.23, 120.60, 68.88, 61.14, 58.16, 54.27, 30.85, 24.95. ESI-MS
    calculated: 310.39; Found: 311.4 [M + H]+ . Anal. (C19 H22 N2 O2 ), C, H, N.

    3.2.8. N-(biphenyl-4-yl)-1-(2-hydroxyethyl)pyrrolidine-2-carboxamide (2g)


    Compound 2g was obtained following the procedure described for 2a, starting from 1g and
    2-bromoethanol. Yield: 69%; oil. 1 H-NMR δ = 9.83 (s, 1H, –NH), 7.73 (d, J = 8.4 Hz, 2H),
    7.57–7.53 (m, 4H), 7.43 (t, J = 7.3, 7.7 Hz, 2H), 7.33 (t, J = 7.3 Hz, 1H), 3.81–3.78 (m, 1H),
    3.75–3.73 (m, 1H), 3.38–3.36 (m, 1H), 3.29–3.28 (m, 1H), 2.92–2.90 (m, 1H), 2.80–2.78 (m, 1H), 2.49–2.47
    (m, 1H), 2.30–2.26 (m, 1H), 2.07–2.05 (m, 1H), 1.86–1.82 (m, 2H); 13 C-NMR δ = 173.36, 140.92, 137.63,
    136.95, 128.97, 128.80, 127.76, 127.04, 119.88, 68.28, 61.09, 57.93, 54.38, 30.89, 24.67. ESI-MS calculated:
    310.39; Found: 311.3 [M + H]+ . Anal. (C19 H22 N2 O2 ), C, H, N.

    3.2.9. N-(4-chlorophenyl)-1-(3-hydroxypropyl)pyrrolidine-2-carboxamide (3a)


    Compound 3a was obtained following the procedure described for 2a, starting from 1a and
    3-bromopropanol. Yield: 82%; oil. 1 H-NMR δ = 9.47 (s, 1H, –NH), 7.60 (d, J = 8.1 Hz, 2H),
    7.27 (d, J = 7.7 Hz, 2H), 3.83–3.76 (m, 2H), 3.30–3.27 (m, 1H), 3.17–3.14 (m, 1H), 2.93–2.86 (m, 1H),
    2.61–2.58 (m, 1H), 2.40–2.33 (m, 1H), 2.30–2.20 (m, 1H), 1.98–1.96 (m, 1H), 1.83–1.78 (m, 4H); 13 C-NMR
    δ = 173.20, 136.83, 131.47, 129.13, 120.86, 68.92, 61.39, 53.95, 53.14, 31.26, 30.71, 24.36. ESI-MS calculated:
    282.77; Found: 283.3 [M + H]+ . Anal. (C14 H19 ClN2 O2 ), C, H, N.

    3.2.10. N-(4-hexylphenyl)-1-(3-hydroxypropyl)pyrrolidine-2-carboxamide (3b)


    Compound 3b was obtained following the procedure described for 2a, starting from 1b and
    3-bromopropanol. Yield: 56%; oil. 1 H-NMR δ = 9.65 (s, 1H, –NH), 7.53 (d, J = 8.1 Hz, 2H),
    7.11 (d, J = 8.1 Hz, 2H), 3.78–3.75 (m, 2H), 3.72–3.70 (m, 1H), 3.33–3.31 (m, 1H), 3.24–3.20 (m, 1H),
    2.88 (t, 2H), 2.74–2.71 (m, 1H), 2.56 (t, 2H), 2.46–2.43 (m, 1H), 2.20–2.25 (m, 1H), 2.01–2.05 (m, 1H),

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