Diethylamine → N,N-Diethyl-4-piperidinecarboxamide

To a stirred solution of 1-tert-butoxycarbonylpiperidine-4-carboxylic acid (5 g, 22.0 mmol) in DMF (100 mL) was added diethyl amine (4.6 mL, 44 mmol), triethylamine (9.1 mL, 66.0 mmol), HOAt (22.0 mL, 0.5 M in DMF, 22.0 mmol) and finally EDCI (8.4 g, 44 mmol). This was allowed to stir for 14 hours at room temperature. The solvent was then removed under reduced pressure. The mixture was taken up in DCM (100 mL). The organic layer was then washed with water (100 mL), 1 N HCl (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. To the organic layer was added TFA (33 mL). The reaction was allowed to stir at room temperature for 2 hours. The solvent was then removed under reduced pressure. The mixture was taken up in DCM (100 mL). The organic layer was then washed with 1 N NaOH (100 mL), water (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was sufficiently pure to use without further purification. The title compound was obtained in 86% yield (3.5 g, 19.0 mmol).

1. customThe solvent was then removed under reduced pressure
2. washThe organic layer was then washed with water (100 mL), 1 N HCl (100 mL), NaCl (sat.) (100 mL)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. additionTo the organic layer was added TFA (33 mL)
6. stirringto stir at room temperature for 2 hours
7. customThe solvent was then removed under reduced pressure
8. washThe organic layer was then washed with 1 N NaOH (100 mL), water (100 mL), NaCl (sat.) (100 mL)
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. customThe solvent was removed under reduced pressure
12. customto use without further purification

ORDレコード

ord-008644b2e28d4b819c68fe384e8ae58c

出典データセット

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08017783B2