Full Papers
doi.org/10.1002/ejoc.202100418
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tography (Diethyl ether/Pentane: 1/99). H NMR (300 MHz, CDCl3) δ
7.48 (d, J=8.5 Hz, 2H), 7.33 (d, J=8.5 Hz, 2H), 4.95 (s, 1H), 2.62 (dq,
J=13.5, 7.1 Hz, 2H), 2.44 (dp, J=13.5, 7.1 Hz, 2H), 1.05 (t, J=7.1 Hz,
6H). 13C NMR (75 MHz, CDCl3) δ 134.4, 133.3, 128.9 (2 C), 128.7 (2 C),
115.9, 57.6, 44.9 (2 C), 13.1 (2 C).
2-(4-Methoxyphenyl)-2-(piperidin-1-yl)acetonitrile (17):[4] Ob-
tained as white solid (m=210.1 mg, 73% yield). Purification by
flash chromatography (Diethyl ether/Pentane: 3/97 to 5/95). 1H
NMR (400 MHz, CDCl3) δ 7.44–7.42 (m, 2H), 6.91–6.89 (m, 2H), 4.75
(s, 1H), 3.81 (s, 3H), 2.53 À 2.46 (m, 4H), 1.64–1.45 (m, 6H). 13C NMR
(100 MHz, CDCl3) δ 159.7, 128.9 (2 C), 125.5, 115.7, 113.8 (2 C), 62.3,
55.2, 50.7 (2 C), 25.7 (2 C), 23.9.
2-(Diethylamino)-2-(4-methoxyphenyl)acetonitrile (10):[20] Ob-
tained as yellow solid (m=177.3 mg, 65% yield). Purification by
flash chromatography (Diethyl ether/Pentane: 2/98 to 3/97). 1H
NMR (300 MHz, CDCl3) δ 7.38 (d, J=8.8 Hz, 2H), 6.67 (d, J=8.8 Hz,
2H), 4.48 (s, 1H), 3.21 (s, 3H), 2.44 (dq, J=13.2, 7.2 Hz, 2H), 2.25 (dq,
J=13.2, 7.2 Hz, 2H), 0.75 (t, J=7.2 Hz, 6H). 13C NMR (75 MHz, CDCl3)
δ 159.8, 128.9 (2 C), 126.6, 116.7, 114.0 (2 C), 57.6, 55.3, 44.7 (2 C),
13.1 (2 C).
3-Phenyl-2-(piperidin-1-yl)propanenitrile (18):[23] Obtained as col-
orless oil (m=155.4 mg, 58% yield). Purification by flash chroma-
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tography (Diethyl ether/Pentane: 5/95 to 10/90). H NMR (400 MHz,
CDCl3) δ 7.19–7.28 (m, 5H), 3.55 (dd, J=8.0, 8.6 Hz, 1H), 2.95–2.98
(m, 2H), 2.62–2.67 (m, 2H), 2.36–2.41 (m, 2H), 1.44–1.62 (m, 6H). 13C
NMR (100 MHz, CDCl3) δ 136.2, 129.2 (2 C), 128.7 (2 C), 127.3, 116.7,
61.3, 51.1 (2 C), 37.7, 25.8 (2 C), 24.0.
2-(Diethylamino)-3-phenylpropanenitrile (11):[4] Obtained as color-
less oil (m=121.3 mg, 48% yield). Purification by flash chromatog-
raphy (Diethyl ether/Pentane: 5/95 to 7/93). 1H NMR (300 MHz,
CDCl3) δ 7.40–7.22 (m, 5H), 3.81 (t, J=7.5 Hz, 1H), 3.03 (d, J=7.5 Hz,
2H), 2.78 (dq, J=13.8, 7.0 Hz, 2H), 2.48 (dq, J=13.8, 7.0 Hz, 2H), 1.09
(t, J=7.0 Hz, 6H). 13C NMR (75 MHz, CDCl3) δ 136.4, 129.3 (2 C),
128.7 (2 C), 127.3, 118.0, 56.6, 45.4 (2 C), 38.6, 13.3 (2 C).
2-Phenyl-2-(piperidin-1-yl)acetonitrile (19):[4] Obtained as yellow
oil (m=182.7 mg, 73% yield). Purification by flash chromatography
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(Diethyl ether/Pentane: 1/99 to 3/97). H NMR (400 MHz, CDCl3) δ
7.58–7.52 (m, 2H), 7.42–7.34 (m, 3H), 4.81 (s, 1H), 2.56–2.47 (m, 4H),
1.68–1.41 (m, 6H). 13C NMR (100 MHz, CDCl3) δ 133.6, 128.6, 128.5
(2 C), 127.7 (2 C), 115.5, 62.9, 50.8 (2 C), 25.7 (2 C), 23.9.
2-(Dibutylamino)-2-(4-methoxyphenyl)acetonitrile (12): Obtained
as white solid (m=247.0 mg, 72% yield). Purification by flash
chromatography (Diethyl ether/Pentane: 2/98). 1H NMR (300 MHz,
CDCl3) δ 7.43 (d, J=8.7 Hz, 2H), 6.90 (d, J=8.7 Hz, 2H), 4.94 (s, 1H),
3.81 (s, 3H), 2.59-2.49 (m, 2H), 2.43–2.35 (m, 2H), 1.45–1.38 (m, 4H),
1.35–1.15 (m, 4H), 0.85 (t, J=7.2 Hz, 6H). 13C NMR (100 MHz, CDCl3)
δ 159.7, 128.9 (2 C), 126.5, 116.4, 113.8 (2 C), 58.1, 55.2, 50.6 (2 C),
29.8 (2 C), 20.2 (2 C), 13.8 (2 C). FTIR (neat): ν=1510, 1249, 1175,
1034, 908, 729 cmÀ 1. HRMS (ESI): m/z calcd for C17H27N2O: [M+H]+:
275.2123; found: 275.2118.
2-Cyclopentyl-2-(piperidin-1-yl)acetonitrile (20): Obtained as col-
orless oil (m=188.2 mg, 78% yield). Purification by flash chroma-
tography (Diethyl ether/Pentane: 1/99). H NMR (400 MHz, CDCl3) δ
3.07 (d, J=10.8 Hz, 1H), 2.61–2.55 (m, 2H), 2.34–2.29 (m, 2H), 2.26–
2.21 (m, 1H), 1.93–1.85 (m, 1H), 1.76–1.68 (m, 1H), 1.63–1.49 (m, 9H),
1.45–1.38 (m, 3H). 13C NMR (100 MHz, CDCl3) δ 117.3, 64.1, 51.1
(2 C), 40.3, 30.6, 29.7, 25.8 (2 C), 25.0, 24.9, 24.1. FTIR (neat): ν=
2938, 1453, 1104, 908, 731 cmÀ 1. HRMS (ESI): m/z calcd for C12H21N2:
[M+H]+: 193.1705; found: 193.1699.
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3-Methyl-2-(piperidin-1-yl)butanenitrile (21):[23] Obtained as pale
yellow solid (m=182.8 mg, 88% yield). Purification by flash
chromatography (Diethyl ether/Pentane: 1/99 to 2/98). 1H NMR
(300 MHz, CDCl3) δ 2.93 (d, J=10.8 Hz, 1H), 2.60–2.53 (m, 2H), 2.37–
2.29 (m, 2H), 2.04–1.91 (m, 1H), 1.69–1.53 (m, 4H), 1.51–1.41 (m, 2H),
1.09 (d, J=6.6 Hz, 3H), 0.98 (d, J=6.6 Hz, 3H). 13C NMR (75 MHz,
CDCl3) δ 117.2, 66.3, 51.1 (2 C), 28.9, 25.9 (2 C), 24.3, 20.4, 19.3.
2-(Dibutylamino)-3-phenylpropanenitrile (13):[4] Obtained as color-
less oil (m=226.1 mg, 70% yield). Purification by flash chromatog-
raphy (Diethyl ether/Pentane: 1/99). 1H NMR (400 MHz, CDCl3) δ
7.36–7.24 (m, 5H), 3.78 (t, J=8.0 Hz, 1H), 3.10–2.91 (m, 2H), 2.71–
2.60 (m, 2H), 2.48–2.37 (m, 2H), 1.51–1.20 (m, 8H), 0.91 (t, J=7.4 Hz,
6H). 13C NMR (100 MHz, CDCl3) δ 131.6, 128.6 (2 C), 127.7 (2 C),
125.9, 116.4, 59.4, 50.6 (2 C), 39.5, 29.8 (2 C), 20.2 (2 C), 13.8 (2 C).
2-(Piperidin-1-yl)hexanenitrile (22): Obtained as colorless oil (m=
2-(Diisopropylamino)-2-phenylacetonitrile (14):[21] Obtained as
colorless oil (m=254.2 mg, 94% yield). Purification by flash
chromatography (Diethyl ether/Pentane: 1/99 to 2/98). 1H NMR
(400 MHz, CDCl3) δ 7.56–7.63 (m, 2H), 7.29–7.42 (m, 3H), 4.97 (s, 1H),
3.18 (septet, J=6.9 Hz, 2H), 1.28 (d, J=6.9 Hz, 6H), 1.04 (d, J=
6.9 Hz, 6H). 13C NMR (100 MHz, CDCl3) δ 136.6, 128.5 (2 C), 128.2,
127.2 (2 C), 121.0, 50.9, 46.6 (2 C), 23.3 (2 C), 19.4 (2 C).
182.5 mg, 81% yield). Purification by flash chromatography (Diethyl
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ether/Pentane: 2/98 to 3/97). H NMR (300 MHz, CDCl3) δ 3.41 (dd,
J=9.0, 6.6 Hz, 1H), 2.65–2.58 (m, 2H), 2.40–2.33 (m, 2H), 1.82–1.31
(m, 12H), 0.91 (t, J=7.0 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 117.5,
58.9, 51.0 (2 C), 30.9, 28.3, 25.9 (2 C), 24.2, 22.2, 13.9. FTIR (neat): ν=
2934, 1459, 1168, 1099, 912, 731 cmÀ 1. HRMS (ESI): m/z calcd for
C11H21N2: [M+H]+: 181.1705; found: 181.1703.
N1,N1-Diisopropyl-1-(4-methoxyphenyl)ethane-1,2-diamine (15):
Obtained as yellow oil (m=190.9 mg, 61% yield over two steps).
Purification by flash chromatography (MeOH/DCM: 2/98 to 6/94). 1H
NMR (400 MHz, CDCl3) δ 7.18 (d, J=8.6 Hz, 2H), 6.75 (d, J=8.6 Hz,
2H), 3.80 (t, J=7.4 Hz, 1H), 3.70 (s, 3H), 3.60 (br s, 2H), 3.17 (hept,
J=6.8 Hz, 2H), 2.95 (dd, J=12.8, 7.4 Hz, 1H), 2.79 (dd, J=12.8,
7.4 Hz, 1H), 1.04 (d, J=6.8 Hz, 6H), 0.78 (d, J=6.8 Hz, 6H). 13C NMR
(100 MHz, CDCl3) δ 158.3, 133.9, 129.7 (2 C), 113.4 (2 C), 59.1, 55.0,
45.0 (2 C), 43.7, 24.1 (2 C), 21.9 (2 C). FTIR (neat): ν=2960, 1510,
1247, 1042, 907, 829, 729 cmÀ 1. HRMS (ESI): m/z calcd for C15H27N2O:
[M+H]+: 251.2123; found: 251.2118.
2-(Dibenzylamino)propanenitrile (23):[18] Obtained as white solid
(m=240.9 mg, 77% yield). Purification by flash chromatography
(Diethyl ether/Pentane: 1/99). H NMR (300 MHz, CDCl3) δ 7.52–7.08
(m, 10H), 3.96 (d, J=13.8, 2H), 3.74 (q, J=7.2, 1H), 3.40 (d, J=13.8,
2H), 1.48 (d, J=7.2, 3H). 13C NMR (75 MHz, CDCl3) δ 138.1 (2 C),
128.8 (4 C), 128.7 (4 C), 127.7 (2 C), 118.2, 55.4 (2 C), 47.8, 18.0.
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2-(Dibenzylamino)-3-phenylpropanenitrile (24): Obtained as yel-
low oil (m=190.6 mg, 47% yield). Purification by flash chromatog-
raphy (Diethyl ether/Pentane: 1/99). 1H NMR (400 MHz, CDCl3) δ
7.40–7.30 (m, 13H), 7.15–7.12 (m, 2H), 4.09 (d, J=13.6 Hz, 2H), 3.94
(t, J=8.0 Hz, 1H), 3.53 (d, J=13.6 Hz, 2H), 3.16 (d, J=8.0 Hz, 2H). 13
C
2-(4-Chlorophenyl)-2-(piperidin-1-yl)acetonitrile (16):[22] Obtained
as yellow solid (m=246.5 mg, 84% yield). Purification by flash
chromatography (Diethyl ether/Pentane: 1/99). 1H NMR (400 MHz,
CDCl3) δ 7.45 (d, J=8.5 Hz, 2H), 7.32 (d, J=8.5 Hz, 2H), 4.75 (s, 1H),
2.45 (t, J=5.4 Hz, 4H), 1.66–1.38 (m, 6H). 13C NMR (100 MHz, CDCl3)
δ 134.5, 132.2, 129.0 (2 C), 128.7 (2 C), 115.1, 62.2, 50.8 (2 C), 25.7
(2 C), 23.8.
NMR (100 MHz, CDCl3) δ 137.6 (2 C), 135.7, 129.3 (2 C), 128.6 (5 C),
128.5 (5 C), 127.5 (2 C), 127.2, 117.1, 55.3 (2 C), 54.6, 37.7. FTIR
(neat): ν=1496, 1454, 906, 728, 697 cmÀ 1. HRMS (ESI): m/z calcd for
C23H23N2: [M+H]+: 327.1861; found: 327.1856.
2-(Dibenzylamino)hexanenitrile (25): Obtained as colorless oil
(m=255.8 mg, 70% yield). Purification by flash chromatography
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(Diethyl ether/Pentane: 1/99). H NMR (400 MHz, CDCl3) δ 7.43–7.29
Eur. J. Org. Chem. 2021, 3634–3640
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