The Journal of Organic Chemistry
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6.83 (t, 1 H, J = 8.1 Hz), 6.97 (d, 2 H, J = 8.6 Hz), 7.25À 7.30 (m, 2 H).
13C NMR (CDCl3, 100 MHz) δ 24.3, 25.5, 26.0, 31.1, 33.3, 67.0, 70.0,
115.6, 118.5, 129.0, 151.4. EIMS (m/z) 205 (M+).8i
(m, 2 H), 4.28 (t, 1 H, J = 5.3 Hz), 6.78 (d, 1 H, J = 7.4 Hz), 6.93 (d, 2 H,
J = 7.4 Hz), 7.22À7.37 (m, 5 H). 13C NMR (CDCl3, 75 MHz) δ 19.5,
63.5, 66.4, 122.4, 126.4, 127.5, 128.1, 129.1, 129.5, 141.5, 144.9. EIMS
(m/z) 241 (M+).4c
trans-2-(Pyrrolidin-1-yl)cyclohexanol (entry 15, Table 3).
1H NMR (CDCl3, 400 MHz) δ 1.20À1.24 (m, 4 H), 1.71À1.77 (m,
6 H), 2.07À2.10 (m, 1 H), 2.45À2.68 (m, 5 H), 3.31À3.35 (m, 1 H).
EIMS (m/z) 169 (M+).6e
2-(2,6-Diisopropylphenylamino)-2-phenylethanol (entry
8, Table 6). H NMR (CDCl3, 400 MHz) δ 0.99 (d, 6 H, J = 6.8
1
Hz), 1.91 (d, 6 H, J = 6.8 Hz), 2.33 (bs, 1 H, D2O exchangeable),
3.08À3.16 (m, 2 H), 3.88 (d, 2 H, J = 10.9, 4.9 Hz), 3.98 (d, 2 H, J = 10.9,
6.3 Hz), 4.06 (t, 1 H, J = 5.6 Hz), 7.01À7.05 (m, 3 H), 7.21À7.32 (m, 5
H). 13C NMR (CDCl3, 100 MHz) δ 24.0, 24.1, 27.5, 65.3, 65.9, 123.6,
125.8, 127.1, 127.6, 128.6, 140.6, 141.2, 142.1. EIMS (m/z) 243 (M+).8e
2-(N-Methylphenylamino)-2-phenylethanol (entry 9,
1
trans-2-Morpholinocyclohexanol (entry 16, Table 3). H
NMR (CDCl3, 400 MHz) δ 1.18À1.27 (m, 4 H), 1.71À1.83 (m, 3 H),
2.12À2.21 (m, 2 H), 2.40À2.45 (m, 2 H), 2.70À2.74 (m, 2 H), 3.34À
3.39 (m, 1 H), 3.67À3.76 (m, 4 H). 13C NMR (CDCl3, 100 MHz) δ
22.2, 24.0, 25.4, 33.1, 48.7, 67.5, 68.4, 70.5. EIMS (m/z) 185 (M+).6e
trans-2-(Piperidin-1-yl)cyclohexanol (entry 17, Table 3).
1H NMR (CDCl3, 400 MHz) δ 1.18À1.25 (m, 4 H), 1.43À1.59 (m, 6
H), 1.76À1.78 (m, 3 H), 2.10À2.13 (m, 2 H), 2.28À2.33 (m, 2 H),
2.65À2.67 (m, 2 H), 3.35À3.37 (m, 1 H). EIMS (m/z) 183 (M+).6e
trans-2-(Phenylmethylamino)cyclohexanol (entry 18,
Table 3). 1H NMR (CDCl3, 400 MHz) δ 0.95À1.05 (m, 1 H),
1.18À1.31 (m, 3 H), 1.71À1.74 (m, 2 H), 2.01À2.06 (m, 1 H),
2.15À2.18 (m, 1 H), 2.28À2.34 (m, 2 H), 3.18À3.24 (ddd, 1 H, J =
4.6, 9.9, 10.4 Hz), 3.70 (d, 1 H, J = 12.9 Hz), 3.97 (d, 1 H, J = 12.9 Hz),
7.24À7.35 (m, 5 H). EIMS (m/z) 205 (M+).6e
1
Table 6). H NMR (CDCl3, 400 MHz) δ 2.13 (bs, 1H, D2O ex-
changeable), 4.16 (m, 2 H), 5.11 (dd, 1 H, J = 8.72, 6 Hz), 6.57 (d, 2 H,
J = 8.0 Hz), 6.84 (t, 1 H, J = 7.2 Hz), 6.96 (d, 2 H, J = 7.9 Hz), 7.14À7.16
(m, 2 H), 7.26À7.32 (m, 5 H). 13C NMR (CDCl3, 100 MHz) δ 32.0,
61.6, 64.5, 114.8, 118.3, 127.1, 127.6, 128.5, 129.2, 137.4, 151.1. EIMS
(m/z) 227 (M+).8b
1-Chloro-3-phenylaminopropan-2-ol (entry 2, Table 7). 1H
NMR (CDCl3, 400 MHz) δ 2.62 (bs, 2 H), 3.21À3.27 (dd, 1 H, J = 7.6,
13.8 Hz), 3.363.41 (dd, 1 H, J = 4.4, 13.8 Hz), 3.58À3.70 (m, 2 H),
4.05À4.07 (m, 1 H), 6.66 (d, 2 H, J = 8.1 Hz), 6.76 (t, 1 H, J = 7.5 Hz),
7.20 (t, 2 H, J = 7.8 Hz). 13C NMR (CDCl3, 100 MHz) δ 47.3, 47.6, 69.7,
113.5, 118.5, 129.4, 147.4.6e
2-Phenylamino-2-phenylethanol (entry 1, Table 6). 1H NMR
(CDCl3, 300 MHz) δ 3.76 (dd, 1 H, J = 11.0, 7.0 Hz), 3.94 (dd, 1 H, J =
10.9, 4.0 Hz), 4.51 (dd, 1H, J = 6.9, 4.1 Hz,), 6.57 (d, 2 H, J = 8.0 Hz), 6.67
(t, 1H, J= 7.3 Hz), 7.10 (t, 2 H, J =7.4 Hz), 7.25À7.36 (m, 5 H). 13CNMR
(CDCl3, 75 MHz) δ 59.8, 67.3, 113.8, 117.9, 126.7, 127.6, 128.8, 129.1,
140.1, 147.2. EIMS (m/z) 213 (M+).6e
1-(Phenylamino)-3-phenoxy-2-propanol (entry 3, Table 7).
1H NMR (CDCl3, 400 MHz) δ 3.29À3.34 (dd, 1 H, J = 7.2, 12.2 Hz),
3.43À3.48 (dd, 1 H, J = 4.4, 12.1 Hz), 4.04À4.11 (m, 2 H), 4.25À4.29 (m,
1 H), 6.71 (d, 1 H, J = 7.6), 6.70À6.75 (m, 1 H), 6.95À7.04 (m. Three H),
7.21À7.34 (m, 4 H). 13C NMR (CDCl3, 100 MHz) δ 46.6, 68.8, 70.0,
113.3, 114.5, 118.0, 121.3, 129.3, 129.6, 148.1, 158.4.6e
1-(4-Chlorophenylamino)-3-phenoxy-2-propanol (entry
4, Table 7). White solid, mp 83À85 °C. 1H NMR (CDCl3, 400 MHz)
δ 2.56 (bs, 1 H), 3.28À3.33 (dd, 1 H, J = 6.8, 12.8 Hz), 3.42À3.47 (dd, 1
H, J = 4.4, 12.8 Hz), 3.00À4.07 (m, 3 H), 4.24À4.29 (m, 1 H),
6.68À6.88 (m, 5 H), 7.18À7.28 (m, 4 H). 13C NMR (CDCl3, 100
MHz) δ 46.5, 68.7, 70.4, 113.3, 115.8, 118.1, 3126.2, 129.3, 129.4, 147.9,
157.0.6e
1-(Furan-2-ylmethoxy)-3-phenylaminopropan-2-ol (entry 5,
Table 7). Oil. IR (DCM) (νmax/cmÀ1): 3447, 2919, 1636, 1260, 749.
1H NMR (CDCl3, 400 MHz) δ 3.12À3.17 (dd, 1 H, J = 7.1, 12.8 Hz),
3.27À3.31 (dd, 1 H, J = 4.4, 12.8 Hz), 3.51À3.55 (dd, 1 H, J = 6.4, 9.6
Hz), 3.59À3.62 (dd, 1 H, J = 3.8, 9.6 Hz), 4.00À4.06 (m, 1 H), 4.52 (s, 2
H), 6.35À6.38 (m, 2 H), 6.64 (d, 2 H, J = 7.7 Hz), 6.72À6.75 (t, 1 H, J =
7.3 Hz), 7.17À7.21 (t, 2 H, J = 7.7 Hz), 7.44 (t, 1 H, J = 0.6 Hz). 13C
NMR (CDCl3, 100 MHz) δ 46.5, 65.2, 69.0, 72.2, 109.7, 110.3, 113.2,
117.7, 129.2, 143.0, 148.2, 151.3. EIMS (m/z) 247 (M+). Anal. Calcd for
C14H17NO3: C, 68.00; H, 6.93; N, 5.66. Found: C, 68.05; H, 6.96;
N, 5.70.
2-(4-Methylphenyl)amino-2-phenylethanol (entry 2,
Table 6). 1H NMR (CDCl3, 400 MHz) δ 2.18 (s, 3 H), 3.71 (dd, 1
H, J = 11.0, 7.2 Hz), 3.91 (dd, 1 H, J = 10.8, 4.0 Hz), 4.46 (dd, 1 H, J = 7.4,
4.4 Hz), 6.49 (d, 2 H, J = 8.4 Hz), 6.90 (d, 2 H, J = 8.4 Hz), 7.22À7.31
(m, 5 H). 13C NMR (CDCl3, 100 MHz) δ 20.3, 60.1, 67.3, 114.0, 126.7,
127.1, 127.5, 128, 130, 140.3, 144.9. EIMS (m/z) 227 (M+).6e
2-(4-Chlorophenyl)amino-2-phenylethanol (entry 3, Table 6).
1H NMR (CDCl3, 400 MHz) δ 1.78 (bs, 1 H, D2O exchangeable), 3.71 (dd,
1 H, J = 10.7, 7.2 Hz), 3.92 (dd, 1 H, J = 11.4, 3.6 Hz), 4.42 (dd, 1 H, J = 6.6,
3.3 Hz), 6.45 (d, 2 H, J = 8.2 Hz), 7.02 (d, 2 H, J = 8.2 Hz), 7.22À7.33 (m, 5
H). 13C NMR (CDCl3, 100 MHz) δ 59.9, 67.2, 11.4, 122.4126, 127.7, 128.4,
128.9, 139.6, 145.7. EIMS (m/z) 247 (M+).6e
2-(4-Methoxyphenylamino)-2-phenylethanol (entry 4,
Table 6). 1H NMR (CDCl3, 400 MHz) δ 3.68 (s, 3 H), 3.70 (dd, 1 H,
J = 11.4, 18.7 Hz), 3.89 (dd, 1 H, J = 4.2, 11.1 Hz), 4.41 (dd, 1 H, J = 4.2,
7.4 Hz), 6.52 (d, 2 H, J = 8.9 Hz), 6.79 (d, 2 H, J = 8.9 Hz), 7.23À7.35
(m, 5 H). 13C NMR (CDCl3, 100 MHz) δ 55.7, 60.8, 67.3, 114.7, 115.3,
126.7, 127.5, 128.8, 140.3, 141.3, 152.3. EIMS (m/z) 243 (M+).8e
2-(2-Methoxyphenylamino)-2-phenylethanol (entry 5,
Table 6). 1H NMR (CDCl3, 400 MHz) δ 2.07 (bs, 1 H, D2O
exchangeable), 3.76 (dd, 1 H, J = 10.8, 7.3 Hz), 3.87 (s, 3 H), 3.89À
3.93 (m, 1 H), 4.50 (dd, 1 H, J = 7.9, 4.7 Hz), 5.0 (bs, 1 H, D2O
exchangeable), 6.45 (dd, 1 H, J = 8.1, 1.48 Hz), 6.61À6.78 (m, 3 H),
7.22À7.35 (m, 5 H). 13C NMR (CDCl3, 100 MHz) δ 55.4, 59.8, 67.4,
109.4, 111.5, 117.1, 121.1, 126.7, 127.5, 128.7, 137.0, 140.2, 147.1. EIMS
(m/z) 243 (M+).6a
1-tert-Butoxy-3-phenylaminopropan-2-ol (entry 6, Table 7).
1H NMR (CDCl3, 300 MHz) δ 1.20 (s, 9H), 3.09À3.16 (dd, 1 H, J = 6.8,
12.4 Hz), 3.27 (dd, 1 H, J = 4.2, 12.5 Hz), 3.36À3.50 (m, 3 H), 3.93À 3.96
(m, 1 H), 6.64 (d, 2 H, J = 8.0 Hz), 6.70 (t, 1 H, J = 7.2 Hz), 7.16 (t, 2 H, J =
7.5 Hz).6e
Ethyl 3-phenylaminopropionate (entry 7, Table 7). 1H NMR
(CDCl3, 400 MHz) δ 1.24 (t, 3 H, J = 7.2 Hz), 4.11À4.19 (m, 2 H),
4.63À4.64 (d, 1 H, J = 3.6 Hz), 4.84À4.85 (d, 1 H, J = 3.6 Hz), 6.58À6.67
(m, 3 H), 7.05À7.11 (m, 2 H), 7.20À7.33 (m, 5 H).6e
2-(2-Fluorophenylamino)-2-phenylethanol (entry 6, Table 6).
1H NMR (CDCl3, 400 MHz) δ 2.00 (bs, 1 H, D2O exchangeable), 3.75 (dd,
1 H, J = 7.0, 11.1 Hz), 3.91 (dd, 1 H, J = 4.1, 11.1 Hz), 4.49 (dd, 1 H, J = 4.4,
6.7 Hz), 4.74 (bs, 1 H, D2O exchangeable), 6.45 (t, 1 H, J = 8.6 Hz),
6.56À6.61 (m, 1 H), 6.83 (t, 1 H, J = 7.6 Hz), 6.93À6.98 (m, 1 H), 7.22À
7.35 (m, 5 H). 13C NMR (CDCl3, 100 MHz) δ 59.6, 67.2, 113.62, 113.62,
114.3, 114.5, 117.2, 117.3, 124.44, 124.48, 126.6, 127.7, 128.9, 135.6, 135.7,
139.7, 150.6, 153.0. EIMS (m/z) 231 (M+).37
’ ASSOCIATED CONTENT
S
Supporting Information. Experimental details, scanned
b
spectra, and spectral data of all known and unknown compounds.
This material is available free of charge via the Internet at http://
pubs.acs.org.
2-(2,6-Dimethylphenylamino)-2-phenylethanol (entry 7,
Table 6). H NMR (CDCl3, 300 MHz) δ 2.16 (s, 6 H), 3.88À3.95
1
8778
dx.doi.org/10.1021/jo201473f |J. Org. Chem. 2011, 76, 8768–8780