F
Q. Yang et al.
Paper
Synthesis
13C NMR (100 MHz, CDCl3): δ = 146.9, 134.7, 133.7, 127.1, 126.7,
4-Ethoxy-N-(p-tolyl)aniline (3ac)22i
124.4, 108.8.
Yield: 40.1 mg (88%); white solid; mp 58.5–60.0 °C.
1H NMR (400 MHz, CDCl3): δ = 7.10–6.95 (m, 4 H), 6.90–6.78 (m, 4 H),
5.38 (s, 1 H), 4.01 (q, J = 6.8 Hz, 2 H), 2.28 (s, 3 H), 1.41 (t, J = 7.0 Hz, 3
1-Phenyl-1H-indole (3n)22g
Yield: 12 mg (31%); light yellow oil.
H).
1H NMR (400 MHz, CDCl3): δ = 7.69 (d, J = 7.6 Hz, 1 H), 7.58 (d, J = 8.0
Hz, 1 H), 7.54–7.49 (m, 4 H), 7.35 (d, J = 3.2 Hz, 2 H), 7.23–7.14 (m,
2 H), 6.69 (d, J = 3.2 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 154.2, 142.5, 136.6, 129.8, 129.3,
121.2, 116.6, 115.5, 63.9, 20.5, 14.9.
4-Chloro-N-(p-tolyl)aniline (3ad)22j
1-Phenyl-1H-benzo[d]imidazole (3o)22b
Yield: 10 mg (23%) and 23 mg (54%) (entries 3 and 6, respectively, in
Table 3); white solid; mp 76.5–78.2 °C.
Yield: 38 mg (97%); brown solid; mp 95.3–96.5 °C.
1H NMR (400 MHz, CDCl3): δ = 8.15 (s, 1 H), 7.94–7.85 (m, 1 H), 7.61–
7.51 (m, 5 H), 7.48 (t, J = 7.2 Hz, 1 H), 7.38–7.29 (m, 2 H).
1H NMR (400 MHz, CDCl3): δ = 7.18 (d, J = 8.8 Hz, 2 H), 7.10 (d, J = 8.4
Hz, 2 H), 6.98 (d, J = 8.4 Hz, 2 H), 6.92 (d, J = 8.8 Hz, 2 H), 5.57 (s, 1 H),
2.32 (s, 3 H).
1-Phenylpiperidine (3p)12b
13C NMR (100 MHz, CDCl3): δ = 142.7, 139.8, 131.6, 129.9, 129.2,
Yield: 29 mg (90%); light yellow liquid.
124.7, 119.2, 117.9, 20.69.
1H NMR (400 MHz, CDCl3): δ = 7.27–7.19 (m, 2 H), 6.97–6.90 (m, 2 H),
6.82 (t, J = 7.2 Hz, 1 H), 3.18–3.08 (m, 4 H), 1.74–1.68 (m, 4 H), 1.59–
1.55 (m, 2 H).
4-Fluoro-N-(p-tolyl)aniline (3ae)22k
Yield: 8.0 mg (21%); white solid; mp 49.5–51.2 °C.
1H NMR (400 MHz, CDCl3): δ = 7.07 (d, J = 8.0 Hz, 2 H), 7.01–6.88 (m, 4
H), 6.91 (d, J = 8.4 Hz, 2 H), 5.47 (s, 1 H), 2.30 (s, 3 H).
4-Phenylmorpholine (3q)12b
Yield: 32 mg (99%); light yellow solid; mp 52.7–53.6 °C.
1H NMR (400 MHz, CDCl3): δ = 7.27 (t, J = 8.0 Hz, 2 H), 6.92–6.86 (m,
3 H), 3.84 (t, J = 4.8 Hz, 4 H), 3.13 (t, J = 4.8 Hz, 4 H).
13C NMR (100 MHz, CDCl3): δ = 157.7 (d, J = 240.0 Hz), 141.2, 139.9,
130.6, 130.0, 119.4 (d, J = 7.7 Hz), 117.9 (s), 115.8 (d, J = 22.3 Hz), 20.6.
4-Iodo-N-(p-tolyl)aniline (3eb)22j
N-Cyclohexylaniline (3r)22b
Yield: 49.6 mg (80%); white solid; mp 96.5–97.9 °C.
Yield: 21 mg (60%); yellow liquid.
1H NMR (400 MHz, CDCl3): δ = 7.48 (d, J = 8.8 Hz, 2 H), 7.10 (d, J = 8.0
Hz, 2 H), 6.99 (d, J = 8.4 Hz, 2 H), 6.76 (d, J = 8.4 Hz, 2 H), 5.57 (s, 1 H),
2.32 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 144.0, 139.4, 138.0, 131.9, 130.0,
119.7, 118.5, 81.2, 20.7.
1H NMR (400 MHz, CDCl3): δ = 7.14 (t, J = 7.8 Hz, 2 H), 6.65 (t, J = 7.2
Hz, 1 H), 6.58 (d, J = 8.2 Hz, 2 H), 3.50 (s, 1 H), 3.27–3.22 (m, 1 H), 2.05
(d, J = 12.0 Hz, 2 H), 1.77–1.74 (m, 2 H), 1.66 (d, J = 12.8 Hz, 1 H), 1.41–
1.32 (m, 2 H), 1.26–1.09 (m, 3 H).
N-Butylaniline (3s)22b
N-(p-Tolyl)naphthalen-2-amine (3kb)22e
Yield: 12 mg (39%); light brown liquid.
Yield: 40.6 mg (92%); white solid; mp 92.5–94.0 °C.
1H NMR (400 MHz, CDCl3): δ = 7.17 (t, J = 8.0 Hz, 2 H), 6.68 (t, J = 7.2
Hz, 1 H), 6.60 (d, J = 7.8 Hz, 2 H), 3.59 (s, 1 H), 3.10 (t, J = 7.2 Hz, 2 H),
1.65–1.54 (m, 2 H), 1.49–1.35 (m, 2 H), 0.95 (t, J = 7.2 Hz, 3 H).
1H NMR (400 MHz, CDCl3): δ = 7.80–7.71 (m, 2 H), 7.65 (d, J = 8.0 Hz, 1
H), 7.45–7.36 (m, 2 H), 7.30 (t, J = 7.4 Hz, 1 H), 7.22–7.14 (m, 3 H), 7.11
(d, J = 8.4 Hz, 2 H), 5.77 (s, 1 H), 2.37 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 141.8, 140.2, 134.8, 131.4, 130.0,
129.2, 129.0, 127.7, 126.43, 126.40, 123.2, 119.6, 119.4, 110.4, 20.8.
N-Benzylaniline (3t)22b
Yield: 25 mg (67%); colorless liquid.
1H NMR (400 MHz, CDCl3): δ = 7.38–7.28 (m, 4 H), 7.27–7.23 (m, 1 H),
7.15 (t, J = 8.0 Hz, 2 H), 6.70 (t, J = 7.2 Hz, 1 H), 6.61 (d, J = 8.4 Hz, 2 H),
4.29 (s, 2 H), 3.97 (s, 1 H).
4-(p-Tolyl)morpholine (3qb)22l
Yield: 31.3 mg (96%); white solid; mp 39.5–41.2 °C.
1H NMR (400 MHz, CDCl3): δ = 7.10 (d, J = 8.4 Hz, 2 H), 6.84 (d, J = 8.4
Hz, 2 H), 3.87 (t, J = 4.6 Hz, 4 H), 3.12 (t, J = 4.8 Hz, 4 H), 2.29 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 149.3, 129.7, 129.6, 116.1, 67.0, 50.0,
20.4.
N-Phenylbenzamide (3u)22g
Yield: 9 mg (23%); white solid; mp 164.2–166.7 °C.
1H NMR (400 MHz, CDCl3): δ = 7.88 (d, J = 6.8 Hz, 2 H), 7.81 (s, 1 H),
7.65 (d, J = 7.8 Hz, 2 H), 7.56 (d, J = 6.8 Hz, 1 H), 7.52 (t, J = 7.2 Hz, 2 H),
7.39 (t, J = 7.6 Hz, 2 H), 7.16 (t, J = 7.2 Hz, 1 H).
Funding Information
Di-p-Tolylamine (3ab)22h
We are grateful to the National Natural Science Foundation of China
(No. 21762020), the Natural Science Foundation of Jiangxi Province
(No. 20171BAB203006), and the Open Project Program of Key Labora-
tory of Functional Small Organic Molecule, Ministry of Education, Ji-
Yield: 36 mg (91%); white solid; mp 70.5–71.8 °C.
1H NMR (400 MHz, CDCl3): δ = 7.08 (d, J = 8.2 Hz, 4 H), 6.96 (d, J = 8.0
Hz, 4 H), 5.51 (s, 1 H), 2.31 (s, 6 H).
13C NMR (100 MHz, CDCl3): δ = 141.2, 130.2, 129.8, 118.0, 20.6.
angxi Normal University (No. KLFS-KF-201408).
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–G