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EXAMPLE 2 N-Methyl-N-(2-chloroethyl)amine, hydrochloride salt Hydrogen chloride was bubbled into a stirred solution of 2-(methylamino)ethanol (10 g, 133 mmol) in CH2 Cl2 (25 ml) until the mixture turned wet litmus paper red. The mixture was cooled to 0° C., and thionyl chloride (15.82 g, 133 mmol) was added dropwise. The mixture was allowed to stir overnight at room temperature. The solvent was removed under reduced pressure to give product as a white solid (16.60 g, 96percent yield): mp 95°-100° C.; 1 H NMR (DMSO-d6) 4.00(t, 2H, J=6.28 Hz), 3.36(t, 2H, J=6.29 Hz), 2.81(s, 3H)ppm; IR (KBr) 3400, 2960, 2750, 2420, 1730, 1580, 1460, 1390, 1310, 1270, 1200, 1150, 1165, 1005, 990, 900, 860, 710 cm-1.
87%
With thionyl chloride In chloroform at 0 - 50℃; for 17 h; Inert atmosphere
To a solution of 2-(methylamino)ethanol (400 pL, 5.00 mmol, 1.0 equiv.) in chloroform (50 mL)was added, under argon at 0°C, thionyle chloride (1.09 mL, 15.0 mmol, 3.0 equiv.). After 17 h of stirring at 50°C, the solvent was concentrated until approximatively 10 mL, then diethyl ether (40 mL) was added to precipitate the compound which was collected on a fritglass, washed several times diethyl ether and dried with a vane pump during one night to afford compound A0219 (567 mg, 4.36 mmol) as a white solid in 87percent yield which was used in the next step without further purification. 1H NMR (400 MHz, MeOD) 5 3.91 (t, J = 5.4 Hz, 2H, CH2CI), 3.42 (t, J = 5.4 Hz, 2H, CH2N), 2.77 (s, 3H, CH3N). 13C NMR (100 MHz, MeOD) 551.46 (CH2N), 40.22 (CH2CI), 33.64 (CH3N).
Reference：
[1] Journal of Medicinal Chemistry, 1995, vol. 38, # 14, p. 2672 - 2680
[2] Patent: US5233031, 1993, A,
[3] Chemical and Pharmaceutical Bulletin, 2002, vol. 50, # 7, p. 941 - 959
[4] Journal of the Chemical Society. Dalton Transactions, 2001, # 8, p. 1306 - 1318
[5] Journal of medicinal chemistry, 1992, vol. 35, # 17, p. 3246 - 3253
[6] Patent: WO2015/140337, 2015, A1, . Location in patent: Page/Page column 33
[7] Journal of Medicinal Chemistry, 1998, vol. 41, # 27, p. 5429 - 5444
[8] Journal of the American Chemical Society, 2008, vol. 130, # 15, p. 5052 - 5053
[9] Organometallics, 2012, vol. 31, # 21, p. 7427 - 7433,7
[10] Chemische Berichte, 1905, vol. 38, p. 3132
[11] Patent: WO2007/25889, 2007, A2, . Location in patent: Page/Page column 37; 39-40; 42
[12] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 5, p. 671 - 679
2
[ 62640-03-3 ]
[ 4535-90-4 ]
Yield
Reaction Conditions
Operation in experiment
80%
With sulfuryl dichloride In chloroform at 0℃; for 3 h; Reflux
To a stirred solution of 2-(methylamino)ethanol hydrochloride (29.7 g, 1.0 eq) in 150 mL CHCI3 was added sulfuryl dichloride (41 g, 1.3 eq) dropwise at 0 °C. After refluxing for 3 h, the reaction was cooled to rt. Then solvent was removed in vacuo, the residue was suspended in 100 mL solution (CH2C12: petroleum ether = 1 : 10), and filtered to give the desired product (28 g, 80percent). :H NMR (400 MHz, DMSO-c ) δ 9.24 (brs, 2H), 3.93(t, J= 6.0 Hz, 2H), 3.28 (t, J= 6.0 Hz, 2H), 2.56 (s, 3H).
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