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separated. The organic layer was washed with H2O (2 × 10
mL) and brine (10 mL), dried over Na2SO4, and filtered.
The filtrate was concentrated in vacuo to give N‐
hexylidenehexan‐1‐amine in 48% yield (220 mg, 1.20
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mmol). H NMR (400 MHz) δ 0.87–0.91 (m, 6H), 1.28–1.34
(m, 14H), 1.48–1.60 (m, 4H), 2.20–2.25 (m, 2H), 3.34 (t, 2H,
J = 7.2 Hz) 7.62 (m, 1H); 13C NMR (125 MHz) δ 13.9, 14.0,
22.4, 22.5, 25.7, 26.8, 30.7, 31.4, 31.5, 35.7, 61.4, 164.9.
Hydrogenation of imine (5b) (Scheme 3). A mixture
of 5b (45.8 mg, 250 μmol) and catalyst [10% Pd/C (26.6
mg, 25.0 μmol) or 10% Rh/C (25.7 mg, 250 μmol)] in cy‐
clohexane (0.5 mL) was stirred at 25 °C under an H2 at‐
mosphere (balloon) for a specific time, then passed
through a membrane filter (0.2 μm) to remove the cata‐
lyst. The catalyst on the filter was washed with EtOAc (20
mL).The filtrate was concentrated in vacuo, and then
NMR of the residue was measured.
ASSOCIATED CONTENT
Supporting Information
This material is available free of charge via the Internet at
1H and 13C NMR spectra of all products (PDF).
AUTHOR INFORMATION
Corresponding Authors
* sajiki@gifu‐pu.ac.jp
* monguchi@daiichi‐cps.ac.jp
ORCID
Yasunari Monguchi: 0000‐0002‐2141‐3192
Tomohiro Maegawa: 0000‐0003‐1580‐1110
Yoshinari Sawama: 0000‐0002‐9923‐2412
Hironao Sajiki: 0000‐0003‐2792‐6826
Present Addresses
§Laboratory of Organic Chemistry, Daiichi University of
Pharmacy, 22‐1 Tamagawa‐cho, Minami‐ku, Fukuoka 815‐8511,
Japan.
†Molecular Catalyst Research Center, Chubu University, 1200
Matsumoto‐cho, Kasugai, Aichi 487‐8501, Japan.
¶School of Pharmaceutical Sciences, Kinki University, 3‐4‐1
Kowakae, Higashi‐Osaka 577‐8502, Japan.
Notes
The authors declare no competing financial interests.
ACKNOWLEDGMENT
We sincerely thank N.E. Chemcat Co. for the kind gift of
Pd/Cs and Rh/Cs.
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