The Journal of Organic Chemistry
Page 8 of 12
2H), 4.36 (s, 2H), 4.05 (bs, 1H). 13C{H} NMR (101 MHz,
CDCl3): δ 148.2, 139.5, 129.4, 128.8, 127.6, 127.3, 117.7,
113.0, 48.4. Spectral data is in agreement with published
data.28
(101 MHz, DMSO-d6): δ 134.2, 129.0, 128.5, 128.4, 42.1.
Spectral data is in agreement with published data.34
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(4-Fluorophenyll)methanamine hydrochloride (7b): white
1
solid; 25.6 mg, 80% yield; H NMR (400 MHz, DMSO-d6): δ
N-Benzylethanamine (4e): colorless liquid; 116.3 mg, 86%
8.63 (bs, 3H), 7.54 (s, 2H), 7.20 (s, 2H), 3.93 (s, 2H). 13C{H}
NMR (101 MHz, DMSO-d6): δ 162.1, 131.4, 130.4, 115.3,
41.3. 19F NMR (376 MHz, CDCl3): δ -109.1. Spectral data is in
agreement with published data.35
1
yield; H NMR (400 MHz, CDCl3): δ 7.32 (m, 4H), 7.26 (m,
1H), 3.80 (s, 2H), 2.69 (q, J = 8.0 Hz, 2H), 1.38 (bs, 1H), 1.15
(t, J = 8.0 Hz, 3H). 13C{H} NMR (101 MHz, CDCl3): δ 140.6,
128.4, 128.2, 126.9, 54.1, 43.7, 15.4. Spectral data is in
agreement with published data.29
(4-Chlorophenyl)methanamine hydrochloride (7c): white
9
1
solid; 31.0 mg, 88% yield; H NMR (400 MHz, DMSO-d6): δ
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N-Tetradecylaniline (4h): white solid; 214.9 mg, 74% yield;
1H NMR (400 MHz, CDCl3): δ 7.31 (t, J = 8.0 Hz, 2H), 6.73 (t,
J = 8.0 Hz, 1H), 6.64 (d, J = 8.0 Hz, 2H), 3.58 (bs, 1H), 3.13 (t,
J = 8.0 Hz, 2H), 1.65 (m, 2H), 1.40 (m, 22H), 0.94 (t, J = 8.0
Hz, 3H). 13C{H} NMR (101 MHz, CDCl3): δ 148.6, 129.3,
117.2, 112.8, 44.1, 32.1, 29.8, 29.8, 29.8, 29.8, 29.8, 29.8,
29.7, 29.6, 29.5, 27.3, 22.8, 14.3. Spectral data is in agreement
with published data.30
8.60 (bs, 3H), 7.53 (d, J = 8.0 Hz, 2H), 7.45 (d, J = 8.0 Hz,
2H), 3.98 (s, 2H). 13C{H} NMR (101 MHz, DMSO-d6): δ
133.2, 131.1, 128.6. Spectral data is in agreement with pub-
lished data.34
(4-Bromophenyl)methanamine hydrochloride (7d): white
1
solid; 34.0 mg, 77% yield; H NMR (400 MHz, DMSO-d6): δ
8.67 (s, 3H), 7.58 (s, 2H), 7.48 (s, 2H), 3.97 (s, 2H). 13C{H}
NMR (101 MHz, DMSO-d6): δ 133.5, 131.3, 121.6, 41.4.
Spectral data is in agreement with published data.34
3,4-Dihydro-2H-benzo[b][1,4]oxazine (4m): colorless liq-
1
uid; 96.2 mg, 71% yield; H NMR (400 MHz, CDCl3): δ 6.80
(4-Methoxyphenyl)methanamine hydrochloride (7e): white
(m, 2H), 6.69 (t, J = 8.0 Hz, 1H), 6.61 (d, J = 8.0 Hz, 1H),
4.26 (t, J = 8.0 Hz, 2H), 3.76 (bs, 1H), 3.41 (t, J = 8.0 Hz, 2H).
13C{H} NMR (101 MHz, CDCl3): δ 144.1, 133.7, 121.3, 118.8,
116.8, 115.7, 65.2, 41.0. Spectral data is in agreement with
published data.31
1
solid; 32.0 mg, 92% yield; H NMR (400 MHz, DMSO-d6): δ
8.54 (bs, 3H), 7.46 (s, 2H), 6.96 (s, 2H), 3.90 (s, 3H), 3.76 (s,
3H). 13C{H} NMR (101 MHz, DMSO-d6): δ 159.3, 130.6,
126.2, 113.9, 55.2, 41.6. Spectral data is in agreement with
published data.36
(E)-N-Cyclohexyl-1-phenylmethanimine (5b): colorless liq-
m-Tolylmethanamine hydrochloride (7f): white solid; 23.3
1
uid; 67.0 mg, 99% yield; H NMR (400 MHz, CDCl3): δ 8.32
1
mg, 74% yield; H NMR (400 MHz, DMSO-d6): δ 8.55 (s,
(s, 1H), 7.74 (d, J = 8.0 Hz, 2H), 7.40 (d, J = 8.0 Hz, 3H), 3.20
(m, 1H), 1.85 (m, 2H), 1.67 (m, 5H), 1.33 (m, 3H). 13C{H}
NMR (101 MHz, CDCl3): δ 158.4, 136.3, 130.1, 128.3, 127.8,
69.8, 34.1, 25.4, 24.6. Spectral data is in agreement with pub-
lished data.32
3H), 7.29 (s, 3H), 7.17 (s, 1H), 3.93 (s, 2H), 2.30 (s, 3H).
13C{H} NMR (101 MHz, DMSO-d6): δ 137.6, 134.0, 129.5,
128.9, 128.4, 125.9, 42.1, 20.9. Spectral data is in agreement
with published data.34
Naphthalen-1-ylmethanamine hydrochloride (7g): white
(E)-N-Cyclohexyl-1-(p-tolyl)methanimine (5c): colorless
1
solid; 34.0 mg, 88% yield; H NMR (400 MHz, DMSO-d6): δ
1
liquid; 73.0 mg, 99% yield; H NMR (400 MHz, CDCl3): δ
8.76 (s, 3H), 8.11 (s, 1H), 7.95 (s, 2H), 7.58 (s, 4H), 4.47 (s,
2H). 13C{H} NMR (101 MHz, DMSO-d6): δ 133.0, 130.5,
129.8, 128.8, 128.5, 127.1, 126.6, 126.0, 125.2, 123.3, 38.9.
Spectral data is in agreement with published data.35
8.29 (s, 1H), 7.62 (d, J = 8.0 Hz, 2H), 7.20 (d, J = 8.0 Hz, 2H),
3.17 (m, 1H), 2.37 (s, 3H), 1.84 (m, 2H), 1.65 (m, 5H), 1.32
(m, 3H). 13C{H} NMR (101 MHz, CDCl3): δ 158.3, 140.3,
133.7, 129.0, 127.8, 69.8, 34.2, 25.4, 24.7, 21.2. Spectral data
is in agreement with published data.32
Benzo[b]thiophen-2-ylmethanamine hydrochloride (7h):
1
light yellow solid; 35.0 mg, 88% yield; H NMR (400 MHz,
(E)-N-Cyclohexyl-1-(4-methoxyphenyl)methanimine (5d):
DMSO-d6): δ 8.88 (bs, 3H), 7.98 (d, J = 8.0 Hz, 1H), 7.85 (d, J
= 8.0 Hz, 1H), 7.59 (s, 1H), 7.38 (m, 2H), 4.32 (s, 2H). 13C{H}
NMR (101 MHz, DMSO-d6): δ 139.6, 138.9, 136.7, 125.3,
124.8, 124.6, 123.7, 122.5, 37.4. Spectral data is in agreement
with published data.37
1
colorless liquid; 54.0 mg, 99% yield; H NMR (400 MHz,
CDCl3): δ 8.25 (s, 1H), 7.68 (d, J = 8.0 Hz, 2H), 6.92 (d, J =
8.0 Hz, 2H), 3.83 (s, 3H), 3.15 (m, 1H), 1.83 (m, 2H), 1.65 (m,
5H), 1.32 (m, 3H). 13C{H} NMR (101 MHz, CDCl3): δ 161.1,
157.8, 129.3, 129.3, 113.6, 69.8, 55.1, 34.2, 25.4, 24.7. Spec-
tral data is in agreement with published data.32
2-Phenylethan-1-amine hydrochloride (7i): white solid;
16.8 mg, 54% yield; 1H NMR (400 MHz, DMSO-d6): δ 7.95 (s,
3H), 7.26 (s, 5H), 2.94 (s, 3H). 13C{H} NMR (101 MHz,
DMSO-d6): δ 137.6, 128.7, 128.6, 126.7, 40.0, 33.0. Spectral
data is in agreement with published data.36
(E)-N-Cyclohexyl-1-(4-fluorophenyl)methanimine (5e): col-
orless liquid; 68.0 mg, 92% yield; 1H NMR (400 MHz,
CDCl3): δ 8.27 (s, 1H), 7.72 (dd, J = 8.0, 4.0 Hz, 2H), 7.07 (t,
J = 8.0 Hz, 2H), 3.18 (m, 1H), 1.79 (m, 2H), 1.70 (m, 3H),
1.57 (m, 2H), 1.30 (m, 3H). 13C{H} NMR (101 MHz, CDCl3):
δ 157.2, 129.9, 129.8, 115.6, 115.4, 69.9, 34.3, 25.6, 24.8. 19F
NMR (376 MHz, CDCl3): δ -110.2. Spectral data is in agree-
ment with published data.33
Cyclohexylmethanamine hydrochloride (7j): white solid;
25.7 mg, 86% yield; 1H NMR (400 MHz, DMSO-d6): δ 8.15 (s,
3H), 2.57 (s, 2H), 1.68 (m, 6H), 1.13 (s, 3H), 0.89 (s, 2H).
13C{H} NMR (101 MHz, DMSO-d6): δ 44.3, 35.4, 29.8, 25.7,
25.1. Spectral data is in agreement with published data.36
Phenylmethanamine hydrochloride (7a): white solid; 21.6
1
mg, 76% yield; H NMR (400 MHz, DMSO-d6): δ 8.34 (bs,
((3r,5r,7r)-Adamantan-1-yl)methanamine
(7k): white solid; 11.4 mg, 28% yield; H NMR (400 MHz,
hydrochloride
3H), 7.47 (s, 2H), 7.38 (m, 3H), 3.98 (s, 2H). 13C{H} NMR
1
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