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127.7, 126.9, 45.6, 42.2. The analytical data was found to be and sodium borohydride (38.13 mg, 1.008 mmol) according to
consistent with literature.16
general procedure. Colourless oil (108 mg, 84% yield); 1H-NMR
The (300 MHz, DMSO-d6) d (ppm) major rotamer: 7.91 (s, 1H + NH),
3.57–3.61 (m, 1H), 1.11–1.72 (m, 10H), minor rotamer: 7.96–8.0
N-(4-Methoxybenzyl)formamide (4).
(m, 2H), 3.05–3.07 (m, 1H), 1.11–1.72 (m, 10H); 13C{1H} NMR
(75 MHz, CDCl3) d mixture of rotamers: 163.6, 160.3, 50.9, 47.0,
34.6, 33.0, 25.4, 25.0, 24.7. The analytical data was found to be
consistent with literature.16
title compound was synthesized from 4-methoxy benzylamine
(95.23 mL, 0.728 mmol) and sodium borohydride (27.54 mg,
0.728 mmol) according to general procedure. Brown crystalline
1
ꢀ
solid (108 mg, 90% yield); m.p. 67–70 C; H-NMR (300 MHz,
CDCl3) d (ppm) major rotamer: 8.21 (s, 1H), 7.16–7.28 (m, 2H),
6.85–6.91 (m, 2H), 6.05 (br, 1H), 4.40 (d, J ¼ 5.61 Hz, 2H), 3.80 (s,
3H), minor rotamer: 8.15 (d, J ¼ 12.0 Hz, 1H), 7.16–7.28 (m, 2H),
6.85–6.91 (m, 2H), 6.05 (br, 1H), 4.34 (d, J ¼ 6.3 Hz, 2H), 3.80 (s,
3H); 13C{1H} NMR (75 MHz, DMSO-d6) d mixture of rotamers:
165.2, 161.3, 158.7, 132.0, 131.3, 129.1, 128.8, 114.1, 55.5, 44.4.
The analytical data was found to be consistent with literature.16
Tert-butyl 4-formylpiperazine-1-carboxylate (9).
The title compound was synthesized from 1-boc-piperazine (100 mg,
0.536 mmol) and sodium borohydride (20.27 mg, 0.536 mmol)
according to general procedure. White solid (83 mg, 72% yield); m.p.
108–110 ꢀC; 1H-NMR (300 MHz, CDCl3) d (ppm) mixture of rotamers:
8.07 (s, 1H), 3.33–3.53 (m, 8H), 1.46 (s, 9H); 13C{1H} NMR (75 MHz,
CDCl3) d mixture of rotamers: 160.9, 154.4, 80.5, 45.4, 39.9, 28.3; HRMS
(ESI-TOF) (m/z): [M + Na]+ calcd for C10H18N2O3Na 237.1215; found
237.12095.
(ꢂ)-N-(1-Phenylethyl)formamide (5).
The title
compound was synthesized from (ꢂ)-a-methylbenzylamine
(105.04 mL, 0.825 mmol) and sodium borohydride (31.21 mg,
0.825 mmol) according to general procedure. Brown oil (80 mg,
65% yield); 1H-NMR (300 MHz, DMSO-d6) d (ppm) major
rotamer: 8.54–8.57 (br, 1H), 8.03 (s, 1H), 7.23–7.35 (m, 5H),
Morpholine-4-carbaldehyde (10).
The title
compound was synthesized from morpholine (99.00 mL, 1.147
mmol) and sodium borohydride (43.39 mg, 1.147 mmol)
4.94–5.04 (m, 1H), 1.35 (d, J ¼ 6.99 Hz, 3H), minor rotamer: according to general procedure. Colourless oil (119 mg, 90%
8.30–8.33 (br, 1H), 8.08 (d, J ¼ 11.5 Hz, 1H), 7.23–7.35 (m, 5H), yield); 1H-NMR (300 MHz, CDCl3) d (ppm) 8.04 (s, 1H), 3.63–3.70
(m, 4H), 3.54–3.57 (m, 2H), 3.38 (t, J ¼ 4.8 Hz, 2H); 13C{1H}
NMR (75 MHz, CDCl3) d 159.2, 65.6, 64.8, 44.2, 39.0, 28.0. The
analytical data was found to be consistent with literature.46
4.67–4.72 (m, 1H), 1.41 (d, J ¼ 6.90 Hz, 3H); 13C{1H} NMR (75
MHz, DMSO-d6) d mixture of rotamers: 164.4, 160.5, 145.2,
144.6, 128.9, 128.7, 127.3, 127.2, 126.4, 126.3, 51.2, 47.0, 23.9,
22.9. The analytical data was found to be consistent with
literature.44
N-(4-Aminobenzyl)formamide (11).
The
N-(Pyridin-4-ylmethyl)formamide (6).
The
title compound was synthesized from 4-aminomethyl aniline
(92.76 mL, 0.818 mmol) and sodium borohydride (30.94 mg,
0.818 mmol) according to general procedure. Brown oil
(101 mg, 82% yield); 1H-NMR (300 MHz, CDCl3) d (ppm) major
rotamer: 8.21 (s, 1H), 7.07 (d, J ¼ 8.4 Hz, 2H), 6.64 (d, J ¼ 8.4 Hz,
2H), 5.67–5.70 (br, 1H), 4.35 (d, J ¼ 5.7 Hz, 2H), 3.68 (br, 2H),
minor rotamer: 8.17 (d, J ¼ 12.1 Hz, 1H), 7.02 (d, J ¼ 8.4 Hz, 2H),
6.64 (d, J ¼ 8.4 Hz, 2H), 4.29 (d, J ¼ 6.3 Hz, 2H); 13C{1H} NMR
(75 MHz, CDCl3) d mixture of rotamers: 164.5, 160.9, 146.0,
129.2, 128.3, 127.3, 115.3, 115.2, 45.3, 41.8; HRMS (ESI-TOF) (m/
z): [M + H]+ calcd for C8H11N2O 151.0871; found 151.12318.
title compound was synthesized from 4-aminomethyl pyridine
(93.89 mL, 0.924 mmol) and sodium borohydride (34.95 mg,
0.924 mmol) according to general procedure. Colourless oil
(114 mg, 90% yield); 1H-NMR (300 MHz, DMSO-d6) d (ppm)
mixture of rotamers: 8.61 (br, 1H), 8.49–8.51 (m, 2H), 8.19 (d, J ¼
1.41 Hz, 1H), 7.25–7.27 (m, 2H), 4.33 (d, J ¼ 6.2 Hz, 2H); 13C
{1H} NMR (75 MHz, DMSO-d6) d mixture of rotamers: 165.6,
161.9, 150.6, 150.1, 149.0, 148.4, 122.5, 121.8, 43.9; HRMS (ESI-
TOF) (m/z): [M + H]+ calcd for C7H9N2O 137.0715; found
137.07112.
N-Butylformamide (7).
The title compound
(ꢂ)-N-(1-Hydroxybutan-2-yl)formamide (12).
The
was synthesized from N-butyl amine (135.13 mL, 1.367 mmol)
and sodium borohydride (51.71 mg, 1.367 mmol) according to
general procedure. Colourless oil (125 mg, 90% yield); 1H-NMR
(300 MHz, CDCl3) d (ppm) major rotamer: 8.15 (s, 1H), 5.58 (br,
1H), 3.20–3.33 (m, 2H), 1.47–1.53 (m, 2H), 1.24–1.39 (m, 2H),
0.92 (t, J ¼ 7.2 Hz, 3H), minor rotamer: 8.03 (d, J ¼ 12.03 Hz, 1H)
5.58 (br, 1H), 3.20–3.33 (m, 2H), 1.47–1.53 (m, 2H), 1.24–1.39
(m, 2H), 0.92 (t, J ¼ 7.2 Hz, 3H); 13C{1H} NMR (75 MHz, CDCl3)
d mixture of rotamers: 164.6, 161.2, 41.4, 37.9, 33.2, 31.5, 20.0,
19.5, 13.7, 13.5. The analytical data was found to be consistent
with literature.17,45
title compound was synthesized from (ꢂ)-2-aminobutan-1-ol
(106.04 mL, 1.121 mmol) and sodium borohydride (42.40 mg,
1.121 mmol) according to general procedure. Colourless oil
(118 mg, 90% yield); 1H-NMR (300 MHz, CDCl3) d (ppm) major
rotamer: 8.18 (d, J ¼ 1.2 Hz, 1H), 6.07 (br, 1H), 3.91–3.92 (m,
1H), 3.47–3.71 (m, 2H), 1.45–1.61 (m, 2H), 0.94 (t, J ¼ 7.4 Hz,
3H), minor rotamer: 8.02 (d, J ¼ 11.9 Hz, 1H), 6.36 (br, 1H),
3.47–3.71 (m, 2H), 3.27–3.29 (m, 1H), 1.45–1.61 (m, 1H), 0.94 (t, J
¼ 7.4 Hz, 3H); 13C{1H} NMR (75 MHz, CDCl3) d mixture of
rotamers: 165.6, 162.3, 64.7, 64.2, 56.8, 24.5, 24.0, 10.46; HRMS
N-Cyclohexylformamide (8).
The title compound
was synthesized from cyclohexyl amine (115.60 mL, 1.008 mmol)
25784 | RSC Adv., 2021, 11, 25777–25787
© 2021 The Author(s). Published by the Royal Society of Chemistry