A. Yıldırım
N-Hexadecylpropanamide (1 h, C19H39NO)
Mg(0)
RCOO Mg2+
2
2RCOOH
H2
White solid; yield 98 %; m.p.: 68–69 °C; FT-IR (ATR):
v = 3,309, 2,917, 2,849, 1,638, 1,548, 1,472, 1,375, 1,283,
1,268, 1,248, 1,231, 1,209, 1,188, 1,158, 1,119, 1,081,
1,057, 1,016, 992, 955, 921, 892, 719, 698 cm-1; 1H NMR
(400 MHz, CHCl3): d = 5.55 (br s, 1H), 3.24 (q, 2H,
J = 7.2 Hz), 2.20 (q, 2H, J = 7.6 Hz), 1.49 (quin, 2H,
J = 6.8 Hz), 1.28–1.25 (m, 26H), 1.16 (t, 3H, J = 7.6 Hz),
0.88 (t, 3H, J = 7.2 Hz) ppm; 13C NMR (100 MHz,
CDCl3): d = 173.70, 39.52, 31.92, 29.78, 29.69, 29.65,
29.58, 29.55, 29.36, 29.31, 26.92, 22.70, 14.13, 9.96 ppm.
In catalytic amount
Lewis acid
R
Mg2+
OOCR
H
O
OH
O
~
H
OH
NH
Ph
Ph
OH
H2N Ph
R
-H2O
R
N
H
-RCOOH
N-Octylhexadecanamide (1i)
White solid; yield 99 %; m.p.: 77–78 °C (Ref. [59]
78–79 °C).
O
R
Ph
N
H
N-Dodecylhexadecanamide (1j)
White solid; yield 99 %; m.p.: 85–86 °C (Ref. [59]
86–87 °C).
Fig. 1 Proposed reaction mechanism
N-Phenyldodecanamide (1a)
White bright needles; yield 79 %; m.p.: 79–80 °C (Ref.
[53, 54] 77–78, 79–80 °C).
References
1. Yehia AH, Bialer M (1990) J Pharm Sci 79:719
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Jagerovic N, Elguero J, Rodriguez AG, Granda SG, Suaridaz M,
De Fonseca FR (2008) Bioorg Med Chem 16:10098
3. De Petrocellis L, Melck D, Bisogno T, Di Marzo V (2000) Chem
Phys Lipids 108:191
4. Da Ros Montes D’Oca C, Coelho T, Marinho TG, Hack CRL, Da
Costa Duarte R, Da Silva PA, Montes D’Oca MG (2010) Bioorg
Med Chem Lett 20:5255
N-(p-Tolyl)dodecanamide (1b)
White bright needles; yield 83 %; m.p.: 83–84 °C (Ref.
[37, 54] 83–84, 85–86 °C).
N-(p-Methoxyphenyl)dodecanamide (1c)
Gray bright crystals; yield 72 %; m.p.: 105–106 °C (Ref.
[54, 55] 104–105, 90–92 °C).
N-Benzyldodecanamide (1d)
White bright crystals; yield 79 %; m.p.: 83.5–84.5 °C (Ref.
[56] 82 °C).
5. Almeida B, Joglar J, Rojas MJL, Decara JM, Silva FJB, Gonzalez
MM, Fito M, Cuevas MR, Farre M, Covas MI, De Fonseca FR,
De la Torre R (2010) ChemMedChem 5:1781
6. Dang HT, Kang GJ, Yoo ES, Hong J, Choi JS, Kim HS, Chung
HY, Jung JH (2011) Bioorg Med Chem 19:1520
7. Magne FC, Mod RR, Sumrell G (1974) J Am Oil Chem Soc
51:93
N-(Naphthalen-1-yl)dodecanamide (1e, C22H31NO)
Gray solid; yield 67 %; m.p.: 106–107 °C; FT-IR (ATR):
v = 3,310, 3,028, 2,917, 2,850, 1,659, 1,595, 1,525, 1,464,
1,405, 1,373, 1,351, 1,329, 1,310, 1,295, 1,270, 1,250,
¨
8. Yıldırım A, Oztu¨rk S, C¸ etin M (2013) J Surfact Deterg 16:13
¨
9. Oztu¨rk S, Yıldırım A, C¸ etin M, Tavaslı M (2014) J Surfact Deterg
17:471
1
1,208, 1,181, 1,113, 1,082, 961, 814, 771, 719 cm-1; H
10. Bower S, Kreutzer KA, Buchwald SL (1996) Angew Chem Int
Ed 35:13
11. Ruck RT, Bergman RG (2004) Angew Chem Int Ed 43:5375
12. Li LC, Ren J, Liao TG, Jiang JX, Zhu HJ (2007) Eur J Org Chem
1026
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Chem Commun 3:301
14. Raja EK, DeShepper DJ, Lill SON, Klumpp DA (2012) J Org
Chem 77:5788
NMR (400 MHz, CHCl3): d = 7.97 (s, 1H), 7.86–7.85 (m,
2H), 7.67 (d, 2H, J = 8.0 Hz), 7.49–7.41 (m, 3H), 2.46 (t,
2H, J = 7.2 Hz), 1.77 (quin, 2H, J = 6.8 Hz), 1.40–1.27
(m, 16H), 0.88 (t, 3H, J = 6.8 Hz) ppm; 13C NMR
(100 MHz, CDCl3): d = 172.15, 134.08, 132.30, 128.72,
127.30, 126.20, 125.93, 125.78, 125.71, 121.22, 120.73,
37.65, 31.93, 29.64, 29.55, 29.42, 29.37, 25.91, 22.72,
14.16 ppm.
15. Bistline RG, Maurer EW, Smith FD, Linfield WM (1980) J Am
Oil Chem Soc 57:98
16. Cvetovich RJ, DiMichele L (2006) Org Process Res Dev 10:944
17. Narasimhan B, Narang R, Judge V, Ohlan R, Ohlan S (2007)
Arkivoc xv:112
18. Buijnsters PJJA, Rodriguez CLG, Willighagen EL, Sommerdijk
NAJM, Kremer A, Camilleri P, Feiters MC, Nolte RJM, Zwa-
nenburg B (2002) Eur J Org Chem 1397
N-Phenylundec-10-enamide (1f)
Slightly brown solid; yield 94 %; m.p.: 65–66 °C (Ref.
[57] 67–68 °C).
N-Benzylundec-10-enamide (1 g)
1
White crystals; yield 96 %; m.p.: 62–63 °C; the H NMR
spectrum agrees with the one given in [58].
19. Yao LY, Lin Q, Niu YY, Deng KM, Zhang JH, Lu Y (2009)
Molecules 14:4051
123