(75 MHz, CDCl3) δ = 158.08, 153.14, 142.27, 134.40, 132.15, 129.66, 121.16, 119.50, 116.30,
113.94, 107.33, 60.59, 55.32, 52.36, 49.87, 42.28, 32.75, 32.69, 31.50, 28.95, 26.75, 22.56,
14.04 ppm. HRMS m/z [M + H]+ calcd for C27H39N4O: 435.3118, found: 435.3109.
4.1.6.7. N-(1-(4-Methoxyphenethyl)piperidin-4-yl)-1-octyl-1H-benzo[d]imidazol-2-amine
1
(10g). This was obtained as a white solid (133 mg, 72%). H NMR (300 MHz, MeOD) δ =
7.30 (dd, J = 6.8, 1.8 Hz, 1H), 7.15 – 6.94 (m, 5H), 6.87 – 6.78 (m, 2H), 3.97 (t, J = 7.1 Hz,
2H), 3.88 – 3.77 (m, 1H), 3.74 (s, 3H), 3.13 (d, J = 11.5 Hz, 2H), 2.83 – 2.72 (m, 2H), 2.71 –
2.57 (m, 2H), 2.37 (t, J = 11.1 Hz, 2H), 2.12 (d, J = 11.9 Hz, 2H), 1.80 – 1.58 (m, 4H), 1.26
(d, J = 11.2 Hz, 10H), 0.87 (t, J = 6.7 Hz, 3H) ppm. 13C NMR (75 MHz, MeOD) δ = 159.70,
154.98, 142.62, 135.33, 132.61, 130.60, 122.10, 120.65, 115.87, 114.99, 108.80, 61.37, 55.64,
53.61, 51.04, 42.68, 32.95, 32.85, 32.58, 30.39, 30.28, 29.68, 27.71, 23.64, 14.42 ppm.
HRMS m/z [M + H]+ calcd for C29H42N4O: 463.3431, found: 463.3429.
4.1.6.8. 1-Decyl-N-(1-(4-methoxyphenethyl)piperidin-4-yl)-1H-benzo[d]imidazol-2-amine
1
(10h). This was obtained as a white solid (122 mg, 62%). H NMR (300 MHz, CDCl3) δ =
7.48 (dt, J = 7.7, 1.0 Hz, 0H), 7.16 – 7.00 (m, 5H), 6.87 – 6.79 (m, 2H), 4.12 – 3.94 (m, 2H),
3.83 (t, J = 7.2 Hz, 2H), 3.78 (s, 3H), 2.97 (d, J = 11.9 Hz, 2H), 2.82 – 2.71 (m, 2H), 2.65 –
2.54 (m, 2H), 2.36 – 2.17 (m, 4H), 1.78 – 1.53 (m, 4H), 1.40 – 1.20 (m, 15H), 0.88 (t, J = 6.7
Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ = 158.07, 153.16, 142.39, 134.45, 132.34, 129.67,
121.16, 119.48, 116.39, 113.94, 107.32, 60.74, 55.34, 52.43, 49.93, 42.31, 32.96, 32.89, 31.92,
29.57, 29.53, 29.38, 29.33, 29.03, 27.13, 22.73, 14.18 ppm. HRMS m/z [M + H]+ calcd for
C31H47N4O: 491.3744, found: 491.3736.
4.1.6.9. 1-Isopentyl-N-(1-(4-methoxyphenethyl)piperidin-4-yl)-1H-benzo[d]imidazol-2-
amine (10i). This was obtained as a white solid (79 mg, 47%). 1H NMR (300 MHz, MeOD) δ
= 7.28 (dd, J = 6.6, 2.2 Hz, 1H), 7.16 – 6.92 (m, 5H), 6.87 – 6.72 (m, 2H), 4.05 – 3.89 (m,
2H), 3.85 – 3.62 (m, 4H), 3.09 (d, J = 11.7 Hz, 2H), 2.82 – 2.65 (m, 2H), 2.65 – 2.47 (m, 2H),
2.28 (t, J = 12.0 Hz, 2H), 2.11 (d, J = 12.0 Hz, 2H), 1.77 – 1.44 (m, 5H), 0.97 (d, J = 6.2 Hz,
6H) ppm. 13C NMR (75 MHz, MeOD) δ = 159.67, 155.11, 142.95, 135.28, 133.20, 130.57,
122.05, 120.57, 115.98, 115.00, 108.68, 61.74, 55.69, 53.76, 51.34, 41.25, 38.33, 33.32, 32.92,
26.97, 22.95 ppm. HRMS m/z [M + H]+ calcd for C26H36N4O: 421.2962, found: 421.2963.
4.1.6.10.
1-(2-Ethylbutyl)-N-(1-(4-methoxyphenethyl)piperidin-4-yl)-1H-
benzo[d]imidazol-2-amine (10j). This was obtained as a white solid (94 mg, 54%). 1H NMR
(300 MHz, MeOD) δ = 7.31 (dd, J = 6.9, 1.9 Hz, 1H), 7.18 – 6.94 (m, 5H), 6.89 – 6.76 (m,
2H), 3.96 – 3.79 (m, 3H), 3.77 (s, 3H), 3.17 (d, J = 11.9 Hz, 2H), 2.86 – 2.75 (m, 2H), 2.74 –
2.63 (m, 2H), 2.41 (t, J = 11.8 Hz, 2H), 2.14 (d, J = 11.9 Hz, 2H), 1.94 – 1.83 (m, 1H), 1.81 –