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ChemicalBook CAS DataBase List 4-FORMYL-N-CBZ-PIPERIDINE
138163-08-3

4-FORMYL-N-CBZ-PIPERIDINE synthesis

11synthesis methods
-

Yield:138163-08-3 100%

Reaction Conditions:

with triethylamine in dichloromethane;dimethyl sulfoxide

Steps:

26.c 26c.
26c. Phenylmethyl 4-formylpiperidinecarboxylate To a stirred solution of oxalyl chloride (2M solution in dichloromethane, 10.9 mL, 21.9 mmol) was added DMSO (3.1 mL, 3.4 g, 43.8 mmol) in dichloromethane (6 mL) over a period of 15 minutes. The product of Example 26b (4.4 g, 17.5 mmol) in dichloromethane (7 mL) was then added at -78° C. over a period of 15 minutes. The resultant solution was stirred at -78° C. for 1 hour and then triethylamine (12.2 mL, 8.86 g, 87.5 mmol) was added, dropwise, over a period of 15minutes. The mixture was further stirred at -78° C. for 30 min and then at 0° C. for 15 min. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic phase was washed with 1% HCl, water, dried over sodium sulfate, filtered and evaporated to give the title compound (4.4 g, 100%) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ9.65 (s, 1H), 7.28-7.38 (m, 5H), 5.12 (s, 2H), 4.04 (br d, J=13.1 Hz, 2H), 2.97-3.06 (m, 2H), 2.38-2.45 (m, 1H), 1.88-1.92 (m,2H), 1.52-1.64 (m, 2H). 13C NMR (75 MHz, CDCl3) δ202.7, 155.2, 136.7, 128.5, 128.6, 127.9, 67.2, 47.8, 43.0, 25.1. LRMS (APIMS) m/z 248 (MH+).

References:

Fang, Xinqin;Garvey, David S.;Gaston, Ricky D.;Lin, Chia-En;Ranatunga, Ramani R.;Richardson, Stewart K.;Wang, Tiansheng;Wang, Weiheng;Wey, Shiow-Jyi US2003/203915, 2003, A1

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