4,4-Difluoro-piperidin-1-ylamine synthesis

Yield:811441-26-6 29%

Reaction Conditions:

Stage #1: 4,4-difluoro-1-nitrosopiperidinewith lithium aluminium tetrahydride in tetrahydrofuran at 0; for 1 h;Heating / reflux;
Stage #2: with water in tetrahydrofuran at 0; for 0.5 h;Heating / reflux;

Steps:

14.2

To a solution of the compound obtained in the above step (1) (1.89 g) in tetrahydrofuran was gradually added lithium aluminum hydride (837 mg) under ice-cooling and the mixture was refluxed under heating for 1 hour. To the reaction mixture was added water under ice-cooling and the mixture was refluxed under heating for 30 minutes. After cooling to room temperature, the reaction mixture was filtered through Celite. The filtrate was concentrated in vacuo and to the residue was added an aqueous sodium hydrogencarbonate solution and chloroform. After stirring, the organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to obtain 1 -amino-4,4-difluoropiperidine (500 mg, yield: 29 %) as a pale yellow oil.MS(APCI)m/z; 137 [M+H]⁺

References:

WO2007/46550,2007,A1 Location in patent:Page/Page column 119