- 1
[ 1445-73-4 ]

[ 74-88-4 ]

[ 26822-37-7 ]
Yield | Reaction Conditions | Operation in experiment |
88% |
at 0 - 20℃; for 1.00 h; |
Step 1: Preparation of 1,1-dimethyl-4-oxopiperidinium iodide [Show Image] Methyl iodide (1.6 mL, 26.5 mmol) was added into a solution of 1-methyl-piperidin-4-one (2.0 g, 17.6 mmol) in acetone (10 mL) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour. The precipitate was filtered off and washed with acetone to afford the title compound as an off-white solid (4.0 g, 88 percent). 1H NMR (D2O, 400 MHz): δ 3.38 (t, J=5.8 Hz, 4H), 3.06 (s, 6H), 1.95-2.05 (m, 4H). LCMS (Method D): Mass found (M+ 128.2), Rt (min): 1.19, Area (percent): 95.3 (Max. Chrom.) |
88% |
at 0 - 20℃; for 1.00 h; |
Step 1: Preparation of 1,1-dimethyl-4-oxopiperidinium iodideMethyl iodide (1.6 mL, 26.5 mmol) was added into a solution of 1-methyl-piperidin-4-one (2.0 g, 17.6 mmol) in acetone (10 mL) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour. The precipitate was filtered off and washed with acetone to afford the title compound as an off-white solid (4.0 g, 88 percent). 1H NMR (D20, 400 MHz): δ 3.38 (t, J=5.8 Hz, 4H), 3.06 (s, 6H), 1.95-2.05 (m, 4H). LCMS (Method D): Mass found (M+ 128.2), Rt (min): 1.19, Area (percent): 95.3 (Max. Chrom.) |
Reference:
[1] Journal of Organic Chemistry, 2006, vol. 71, # 22, p. 8602 - 8609
[2] Journal of Organic Chemistry, 2014, vol. 79, # 8, p. 3358 - 3373
[3] Organic Process Research and Development, 2004, vol. 8, # 6, p. 939 - 941
[4] Angewandte Chemie - International Edition, 2008, vol. 47, # 32, p. 5968 - 5972
[5] Journal of the American Chemical Society, 2009, vol. 131, # 1, p. 357 - 367
[6] Patent: EP2508526, 2012, A1. Location in patent: Page/Page column 45
[7] Patent: WO2012/130915, 2012, A1. Location in patent: Page/Page column 55
[8] Journal of Organic Chemistry, 1945, vol. 10, p. 277,278
[9] Journal of the American Chemical Society, 1949, vol. 71, p. 465
[10] Journal of the Chemical Society, 1949, p. 708,712
[11] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1984, # 10, p. 1647 - 1652
[12] Patent: WO2005/90333, 2005, A1. Location in patent: Page/Page column 135
[13] Patent: CN105985355, 2016, A. Location in patent: Paragraph 0692; 0693; 0694; 0695