R. J. Whitby et al.
FULL PAPER
pound 5 (0.480 g, 92%) as a white solid, m.p. 74–75 °C. IR: ν = (CH2), 29.12 (CH2), 25.12 (CH2), 22.49 (CH2), 13.94 (CH3) ppm.
˜
3291 (m), 2916 (m), 1631 (s), 1554 (m), 694 (s) cm–1. 1H NMR
(400 MHz, CDCl3): δ = 7.39–7.26 (m, 5 H), 5.77 (br. s, 1 H, NH),
4.44 (d, J = 5.5 Hz, 2 H), 2.21 (dd, J = 7.3, 7.3 Hz, 2 H), 1.66
(quint, J = 7.6 Hz, 2 H), 1.41–1.23 (m, 12 H), 0.89 (t, J = 6.8 Hz,
3 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 172.95 (C), 138.42
(C), 128.67 (CH), 127.79 (CH), 127.45 (CH), 43.56 (CH2), 36.63
(CH2), 31.84 (CH2), 29.43 (CH2), 29.32 (CH2), 29.30 (CH2), 29.23
(CH2), 25.76 (CH2), 22.64 (CH2), 14.08 (CH3) ppm. HRMS (ESI):
calcd. for C17H28NO [M + H]+ 262.2165; found 262.2161.
MS (ESI+): m/z (%) = 264.3 (100) [M + Na]+, 296.3 (42) [M + Na
+ MeOH]+.
N-Cyclohexyldecanamide (8g): According to continuous-flow pro-
cedure A, cyclohexylamine (1.0 mmol, 114.7 μL) gave compound
8g (0.215 g, 85%) as a white solid, m.p. 71–73 °C. IR: ν = 3297 (m),
˜
1
2917 (m), 1637 (s), 1546 (s) cm–1. H NMR (400 MHz, CDCl3): δ
= 5.17 (br. s, 1 H, NH), 3.66 (m, 1 H), 2.05 (t, J = 8.0 Hz, 2 H),
1.76–1.90 (m, 2 H), 1.63 (dt, J = 14.0, 4.0 Hz, 2 H), 1.40–1.57 (m,
4 H), 0.93–1.38 (m, 16 H), 0.81 (t, J = 6.8 Hz, 3 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 172.22 (C), 48.08 (CH), 37.24 (CH2), 33.39
(CH2), 31.95 (CH2), 29.79 (CH2), 29.54 (CH2), 29.45 (CH2), 29.36
N-(tert-Butyl)decanamide (8b): According to continuous-flow pro-
cedure A, tert-butylamine (1.0 mmol, 105.1 μL) gave compound 8b
(0.218 g, 96%) as a white solid, m.p. 33–35 °C. IR: ν = 3307 (m), (CH2), 25.99 (CH2), 25.66 (CH2), 24.97 (CH2), 22.75 (CH2),
˜
1
2959 (m), 1644 (s), 732 (s) cm–1. H NMR (300 MHz, CDCl3): δ = 14.10 (CH3) ppm. MS (ESI+): m/z (%) = 317.3 (100) [M + Na +
5.25 (br. s, 1 H, NH), 2.07 (t, J = 7.6 Hz, 2 H), 1.59 (quint, J =
7.1 Hz, 2 H), 1.34 (s, 9 H), 1.23–1.37 (m, 12 H), 0.87 (t, J = 6.8 Hz,
3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 172.51 (C), 50.99 (C),
37.75 (CH2), 31.83 (CH2), 29.43 (CH2), 29.35 (CH2), 29.25 (CH2),
29.21 (CH2), 28.83 (CH3), 25.78 (CH2), 22.64 (CH2), 14.07 (CH3)
ppm. HRMS (ESI): calcd. for C14H30NO [M + H]+ 228.2322;
found 228.2318.
MeCN]+.
N-Cyclohexyl-N-methyldecanamide (8h): According to continuous-
flow procedure A, N-methyl-N-cyclohexylamine (0.5 mmol,
65.2 μL) gave compound 8h (0.124 g, 93%) as a yellow oil. IR: ν =
˜
2923 (s), 1640 (s), 1450 (m) cm–1. A rotameric mixture was ob-
served by NMR spectroscopy. Additional rotamer peaks are indi-
cated *. 1H NMR (300 MHz, CDCl3): δ = 4.42 (tt, J = 11.0, 3.0 Hz,
1 H), 3.51 (* tt, J = 11.5, 3.0 Hz, 1 H), 2.79 (s, 3 H), 2.76 (* s, 3
H), 2.29 (t, J = 7.5 Hz, 2 H), 2.25 (* t, J = 7.5 Hz, 2 H), 0.97–1.87
(m, 20 H), 0.85 (t, J = 6.2 Hz, 3 H) ppm. 13C NMR (75 MHz,
N,N-Diisopropyldecanamide (8c):[16] According to continuous-flow
procedure A, diisopropylamine (1.0 mmol, 141.1 μL) gave com-
pound 8c (0.204 g, 80%) as a pale yellow oil. IR: ν = 2923 (m),
˜
1638 (s), 1438 (m) cm–1. 1H NMR (300 MHz, CDCl3): δ = 3.92 (m, CDCl3): δ = 172.60 (C*), 172.56 (C), 56.55 (CH), 51.96 (CH*),
1 H), 3.43 (m, 1 H), 2.22 (t, J = 8.1 Hz, 2 H), 1.56 (quint, J =
7.1 Hz, 2 H), 1.32 (d, J = 7.1 Hz, 6 H), 1.19–1.29 (m, 12 H), 1.15
34.14 (CH2), 33.53 (CH2), 31.78 (CH2), 30.91 (CH2*), 29.82 (CH2),
29.45 (CH2), 29.37 (CH2), 29.18 (CH2), 26.94 (CH3), 25.78 (CH2),
(d, J = 6.6 Hz, 6 H), 0.83 (t, J = 6.7 Hz, 3 H) ppm. 13C NMR 25.57 (CH2), 25.24 (CH2*), 25.10 (CH2), 22.56 (CH2), 13.98 (CH3)
(75 MHz, CDCl3): δ = 171.95 (C), 48.12 (CH), 45.36 (CH), 35.31
ppm. HRMS (ESI): calcd. for C17H34NO [M + H]+ 268.2635;
(CH2), 31.74 (CH2), 29.37 (CH3), 29.17 (CH2), 25.36 (CH2), 22.52 found 268.2629.
(CH2), 20.90 (CH2), 20.58 (CH2), 13.95 (CH3) ppm. MS (ESI+):
N-Phenyldecanamide (8k):[15] According to continuous-flow pro-
cedure A, aniline (1.0 mmol, 91.2 μL) gave compound 8k (0.212 g,
m/z (%) = 278.3 (100) [M + Na]+, 533.5 (35) [2M + Na]+.
1-(Piperidin-1-yl)decan-1-one (8d):[17] According to continuous-flow
procedure A, piperidine (1.0 mmol, 98.8 μL) gave compound 8d
86%) as a white solid, m.p. 63–64 °C. IR: ν = 3313 (m), 2916 (m),
˜
1
1655 (s), 1600 (s), 1538 (s) cm–1. H NMR (300 MHz, CDCl3): δ =
(0.208 g, 87%) as a pale yellow oil. IR: ν = 2923 (s), 1635 (s), 1434
7.55 (br. s, 1 H, NH), 7.45 (d, J = 8.0 Hz, 2 H), 7.21 (t, J = 8.0 Hz,
2 H), 7.00 (t, J = 7.3 Hz, 1 H), 2.26 (t, J = 7.6 Hz, 2 H), 1.63
˜
(m) cm–1. 1H NMR (300 MHz, CDCl3): δ = 3.53 (dd, J = 5.6,
5.6 Hz, 2 H), 3.38 (dd, J = 5.6, 5.6 Hz, 2 H), 2.30 (t, J = 7.7 Hz, 2 (quint, J = 7.3 Hz, 2 H), 1.11–1.32 (m, 12 H), 0.80 (t, J = 6.7 Hz,
H), 1.19–1.36 (m, 8 H), 1.19–1.35 (m, 12 H), 0.87 (t, J = 6.1 Hz, 3
3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 171.69 (C), 138.04
H) ppm. 13C NMR (75 MHz, CDCl3): δ = 171.49 (C), 46.68 (CH2), (C), 128.85 (CH), 124.06 (CH), 119.86 (CH), 37.73 (CH2), 31.80
42.54 (CH2), 33.46 (CH2), 31.83 (CH2), 29.50 (CH2), 29.42 (CH2), (CH2), 29.41 (CH2), 29.35 (2 CH2), 29.24 (CH2), 25.65 (CH2), 22.61
29.23 (CH2), 26.55 (CH2), 25.56 (CH2), 25.47 (CH2), 24.56 (CH2), (CH2), 14.06 (CH3) ppm. MS (ESI+): m/z (%) = 495.5 (20) [2M +
22.61 (CH2), 14.04 (CH3) ppm. MS (ESI+): m/z (%) = 262.3 (100)
Na]+, 517.4 (4) [2M + Na]+.
[M + Na]+, 502.5 (10) [2M + Na]+.
N-Allyl-N-phenyldecanamide (8l): According to continuous-flow
procedure A, N-allylaniline (0.5 mmol, 67.8 μL) gave, after purifi-
1-(Pyrrolidin-1-yl)decan-1-one (8e): According to continuous-flow
procedure A, pyrrolidine (0.5 mmol, 41.1 μL) gave compound 8e
cation on silica, compound 8l (0.132 g, 92%) as a yellow oil. IR: ν
˜
(0.098 g, 86%) as a brown oil. IR: ν = 2922 (m), 1640 (s), 1425 (s) = 2923 (m), 1657 (s), 699 (s) cm–1. H NMR (300 MHz, CDCl3): δ
1
˜
1
cm–1. H NMR (300 MHz, CDCl3): δ = 3.39 (dt, J = 13.5, 6.8 Hz, = 7.39–6.93 (m, 5 H), 6.02–5.66 (m, 1 H), 5.26–4.87 (m, 2 H), 4.21
4 H), 2.21 (t, J = 7.5 Hz, 2 H), 1.74–1.98 (m, 4 H), 1.60 (quint, J (d, J = 6.2 Hz, 2 H), 1.96 (t, J = 7.3 Hz, 2 H), 1.47 (m, 2 H), 0.95–
= 7.3 Hz, 2 H), 1.13–1.34 (m, 12 H), 0.83 (t, J = 6.6 Hz, 3 H) ppm.
1.38 (m, 12 H), 0.80 (t, J = 6.4 Hz, 3 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 173.19 (C), 143.17 (C), 133.77 (CH), 129.85 (CH),
13C NMR (75 MHz, CDCl3): δ = 171.72 (C), 46.48 (CH2), 45.43
(CH2), 34.73 (CH2), 31.74 (CH2), 29.41 (CH2), 29.35 (CH2), 29.16 128.72 (CH), 128.13 (CH), 117.92 (CH2), 52.56 (CH2), 34.74 (CH2),
(CH2), 26.01 (CH2), 24.84 (CH2), 24.30 (CH2), 22.53 (CH2), 13.97 32.22 (CH2), 29.75 (CH2), 29.69 (CH2), 29.64 (CH2), 29.61 (CH2),
(CH3) ppm. HRMS (ESI): calcd. for C14H27NNaO [M + Na]+ 25.87 (CH2), 23.01 (CH2), 14.75 (CH3) ppm. HRMS (ESI): calcd.
248.1985; found 248.1986.
for C19H30NO [M + H]+ 288.2322; found 288.2313.
1-Morpholinodecan-1-one (8f):[18] According to continuous-flow
procedure A, morpholine (0.5 mmol, 43.3 μL) gave compound 8f
N,N-Diallyldecanamide (8m):[19] According to continuous-flow pro-
cedure A, diallylamine (0.5 mmol, 61.7 μL) gave compound 8m
(0.101 g, 84%) as a pale yellow oil. IR: ν = 2922 (m), 1645 (s), 1426
(0.109 g, 87%) as a pale yellow oil. IR: ν = 3298 (br.), 2918 (s),
˜
˜
(m), 1115 (s) cm–1. 1H NMR (300 MHz, CDCl3): δ = 3.49–3.63 (m, 1641 (s), 1552 (s) cm–1. 1H NMR (300 MHz, CDCl3): δ = 5.65–
6 H), 3.36–3.44 (m, 2 H), 2.24 (t, J = 7.7 Hz, 2 H), 1.55 (quint, J 5.81 (m, 2 H), 5.03–5.20 (m, 4 H), 3.95 (m, 2 H), 3.84 (m, 2 H),
= 7.2 Hz, 2 H), 1.12–1.32 (m, 12 H), 0.81 (t, J = 6.5 Hz, 3 H) ppm.
2.27 (t, J = 7.7 Hz, 2 H), 1.61 (quint, J = 7.1 Hz, 2 H), 1.16–1.36
13C NMR (75 MHz, CDCl3): δ = 171.74 (C), 66.80 (CH2), 66.53
(m, 12 H), 0.84 (t, J = 6.6 Hz, 3 H) ppm. 13C NMR (75 MHz,
(CH2), 45.91 (CH2), 41.70 (CH2), 32.97 (CH2), 31.71 (CH2), 29.30 CDCl3): δ = 173.00 (C), 133.36 (CH), 132.91 (CH), 116.87 (CH2),
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© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Eur. J. Org. Chem. 2015, 1491–1499