4-p-Aminophenyl-1-Boc-piperidine

Uses

1-Boc-4-(4-aminophenyl)piperidine is a useful synthetic intermediate used in the synthesis of FMS inhibitors that may be useful in treating rheumatoid arthritis and other chronic inflammatory diseases.

Synthesis

General procedure for the synthesis of tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate from tert-butyl 4-(4-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate: 4-(4-aminophenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.35 g, 1.2 mmol) (prepared in previous step) was dissolved in methanol and added to a 10% Pd/C catalyst and hydrogenated at 20 psi hydrogen pressure for 1 hour. Upon completion of the reaction, the reaction solution was filtered to remove the catalyst and the filtrate was concentrated to give 0.35 g (100% yield) of tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate as a yellow solid. Mass spectrum (ESI, m/z): the calculated value of [M+H]+ for C16H24N2O2 was 277.2 and the measured value was 277.1.

References

[1] Patent: WO2006/47277, 2006, A2. Location in patent: Page/Page column 58-59
[2] Patent: US2006/281788, 2006, A1. Location in patent: Page/Page column 55
[3] Patent: US2008/51402, 2008, A1. Location in patent: Page/Page column 41
[4] Patent: US2008/114007, 2008, A1. Location in patent: Page/Page column 90
[5] Patent: US2007/60577, 2007, A1. Location in patent: Page/Page column 53