ChemicalBook CAS DataBase List N,N-Dimethyl-4-(4-pyridinyl)aniline

N,N-Dimethyl-4-(4-pyridinyl)aniline synthesis

5synthesis methods

Product Name:N,N-Dimethyl-4-(4-pyridinyl)aniline
CAS Number:1137-80-0
Molecular formula:C13H14N2
Molecular Weight:198.26

110-86-1 Synthesis

110-86-1
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121-69-7 Synthesis

121-69-7
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1137-80-0
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Yield:1137-80-0 85%

Reaction Conditions:

Stage #1: pyridinewith 1,3,5-trichloro-2,4,6-triazine at 70; for 0.25 h;
Stage #2: N,N-dimethyl-anilinewith aluminum (III) chloride at 20 - 100; for 4.5 h;

Steps:

4-p-(N,N-Dimethylaminophenyl)pyridine (5)

A solution of cyanuric chloride (22.8 g, 0.124 mol, 0.3 eq) in pyridine (100 mL, 1.24 mol, 3 eq) was heated at 70 °C for 15 min, then cooled. To this solution was added PhNMe2 (52 mL 0.413 mol, 1 eq) followed by AlCl3 (55 g, 0.413 mol, 1 eq) at less than 30 °C and the mixture was stirred for 1.5 h at room temp., heated at 100 °C for 3 h and cooled to room temp. The crude solids were added to 10% HCl (100 mL) and dissolved at above 80 °C. The temperature of the acidic solution was decreased to warm and the solution was filtered through Celite. The acidic filtrates were extracted with methylene chloride (1 L). The aqueous layer was neutralized with sodium hydroxide (NaOH) and extracted with methylene chloride (1 L×2). The organic layer was dried, filtered and evaporated under reduced pressure. The crude solids were dissolved with methylene chloride (500 mL). The suspended solution was evaporated at 0 °C under reduced pressure. The precipitated solids were collected and washed with ether to give pure product 5 as pale pink solid (69.5 g, 85% yield); mp 236 °C (lit.5) 233-234 °C); IR (KBr) νmax cm-1 3436, 2923, 1608, 1592, 1562, 1535, 1493, 1446, 1365, 1293, 1229, 1176; 1H-NMR (250 MHz CDC13) δ: 8.56 (2H, d, J=5.6 Hz), 7.60 (2H, d, J=8.8 Hz), 7.51 (2H, d, J=6.0 Hz), 6.80 (2H, d, J=8.9 Hz), 3.04 (6H, s); 13C-NMR (63 MHz, CDCl3) δ: 140.1, 129.2, 120.7, 112.5, 40.2, 31.1; LC-MS (ESI+) m/z 199.18 [M+H]+ (Calcd for C13H14N2. Found: 198.12). Anal. Calcd for C13H14N2: C, 78.79; H, 7.07; N, 14.14%. Found: C, 78.83; H,7.15; N, 14.07%.

References:

Min, Dongguk;Han, Moon Hi;Lee, Seulki;Jung, Mankil [Chemical and Pharmaceutical Bulletin,2015,vol. 63,# 10,p. 843 - 847]