As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1120-16-7 name is Dodecanamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 1120-16-7
General procedure: For the synthesis of amide carboxylic acid (1-2 mM) wasdissolved in toluene (10 ml) then solution of borane tetrahydrofuran(THF) (1 M) was added at 0 oC. After additionof borane THF complex reaction mixture is kept at roomtemperature for 1 h. DAA was added to the reaction mixtureand reaction mixture refluxed for 5-10 h. Then reactionmixture was cooled to room temperature and acidifies with1M HCl, and extracted with ethyl acetate. Wash with water2-3 times. Organic phase was dried over anhydrous Na2SO4and concentrate under reduced pressure. Purification ofproduct was accomplished by column chromatographyusing silica gel (hexane: ethyl acetate). (+)-N-(dodecanoyl)-dehydroabietylamine (2) Rf: 0.627(hexane/ethylacetate, 9:1) State: gummy, Yield:93.15%, [alpha]D26: -18.42 (C=0.0403, CHCl3), HRMS-ESI:calcd for C32H54NO (M+H)+ 468.4205, found 468.4179,IR (cm-1): 3303 (N-H stretching), 2923 (C-H), 2856(C-H),1647 (C=O), 1548 (N-H bending), 1460 (CH2 bending),1375 (CH3 bending), 719 (CH2 long chain band). UV: lambdamax241, 254, 276. 1HNMR (400MHz, CDCl3) delta ppm: 0.86(3H, t, J = 6.0 Hz, H-12?), 0.98 (3H, s, H-19), 1.23 (24H, Brs, H-16, and 17, 3?-11?), 1.95 (1H, t, J = 5.6 Hz, H-5), 2.32(4H, t, J = 7.6 Hz, H-1, and 2?), 2.86 (2H, m, H-3), 2.98(1H, m, H-15), 3.17 (1H, dd, J = 6.4 and 13.6 Hz, H-18a),3.28 (1H, dd, J = 6.4 and 13.6 Hz, H-18b), 7.28 (1H, d, J =8.0 Hz, H-12), 7.39 (1H, d, J = 8.0 Hz, H-11), 7.83 (1H, s,H-14). 13CNMR (100MHz, CDCl3) delta ppm: 14.1 (C-12?),18.5 (C-2), 18.7 (C-19), 18.9 (C-6), 22.6 (C-11?), 24.7 (C-16 and 17), 25.2 (C-20), 29.5-29.3 (C-3?-9?), 31.8 (C-10?),33.5 (C-15), 33.7 (C-2?), 35.7 (C-3), 37.3 (C-4), 37.4 (C-10), 38.3 (C-1), 44.5 (C-5), 49.7 (C-18), 123.6 (C-12),124.9 (C-11), 132.6 (C-14), 134.7 (C-8), 145.6 (C-13),147.1 (C-9), 173.5 (C-1?).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dodecanamide, and friends who are interested can also refer to it.
Reference:
Article; Mustufa, Muhammad Ayaz; Aslam, Afshan; Ozen, Cigdem; Ali Hashmi, Imran; Naqvi, Naim ul Hasan; Ozturk, Mehmet; Ali, Firdous Imran; Medicinal Chemistry Research; vol. 26; 7; (2017); p. 1367 – 1376;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics