ChemicalBook CAS DataBase List tert-Butyl 2-cyanopiperidine-1-carboxylate

tert-Butyl 2-cyanopiperidine-1-carboxylate synthesis

13synthesis methods

Product Name:tert-Butyl 2-cyanopiperidine-1-carboxylate
CAS Number:153749-89-4
Molecular formula:C11H18N2O2
Molecular Weight:210.27

Acetonitrile (220 mL) and DMF (3.82 mL, 49.4 mmol) were added to a 500 mL round bottom flask equipped with a stir bar. Cooled the mixture down to -5 °C and added oxalyl chloride (24.7 mL, 49.4 mmol, 2 M dichloromethane). The resulting mixture was stirred for 15 min, followed by the addition of a solution of 2-carbamoyl-piperidine-1- carboxylic acid tert-butyl ester (9.4 g, 41.2 mmol) in acetonitrile (50 mL) and pyridine (8.3 mL, 103 mmol). The reaction mixture was left stirring at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (300 mL). The organic phase was successively washed with water (300 mL) and brine (200 mL), dried (sodium sulfate), filtered, and concentrated in vacuo to isolate tert-Butyl 2-cyanopiperidine-1-carboxylate (8.44 g, 97percent) as a yellow solid.

tert-Butyl 2-cyanopiperidine-1-carboxylate

388077-74-5
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$35.93/5g

153749-89-4
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$7.00/250mg

Yield:153749-89-4 97%

Reaction Conditions:

with pyridine;oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane;acetonitrile at -5 - 20;

Steps:

14.a

Acetonitrile (220 mL) and DMF (3.82 mL, 49.4 mmol) were added to a 500 mL round bottom flask equipped with stir bar. Cooled the mixture down to-5°C and to it added oxalyl chloride (24.7 mL, 49.4 mmol, 2 M dichloromethane). The resulting mixture was stirred for 15 min. This was followed by addition of solution of 2-carbamoyl-piperidine-1- carboxylic acid tert-butyl ester (9.4 g, 41.2 mmol) in acetonitrile. (50 mL) and pyridine (8.3 mL, 103 mmol). Reaction mixture was left stirring at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (300 mL). The organic phase was successively washed with water (300 mL) and brine (200 mL), dried (sodium sulfate), filtered and concentrated in vacuo to isolate the title compound (8.44 g, 97%) as a yellow solid. 1H NMR (CDCIs), 8 (ppm): 5.23 (bs, 1H), 4.03 (bs, 1H), 2.93 (t, 1H), 1.75 (m, 5H), 1.46 (m, 10H).

References:

WO2005/80386,2005,A1 Location in patent:Page/Page column 42-43

7677-24-9 Synthesis