4-(3-AMINO-PHENYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

413.2±45.0 °C(Predicted)

Density 

1.100±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.60±0.10(Predicted)

Appearance

White to off-white Solid

4-(3-AMINO-PHENYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

Tert-butyl 4-(3-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (3.10 g, 11.3 mmol) was used as a raw material and mixed with 10% Pd/C (1.00 g) in ethanol (100 mL). The reaction system was hydrogenated at room temperature for 2 days using the balloon method. After completion of the reaction, the mixture was filtered through diatomaceous earth and the filter cake was washed with ethanol. The ethanol extracts were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with the eluent dichloromethane:methanol:isopropylamine (95:5:1, v/v/v) to afford the target product tert-butyl 4-(3-aminophenyl)-piperidine-1-carboxylate (2.63 g, 84% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.10 (t, 1H, J = 7.6 Hz), 6.62 (d, 1H, J = 8.4 Hz), 6.60-6.59 (m, 2H), 4.27-4.18 (m, 2H), 3.62-3.58 (m, 2H), 2.80-2.72 (m, 2H), and 2.62-2.59 (m, 1H), 1.89-1.52 (m, 4H), 1.49 (s, 9H); ESMS m/e: 277.2 (M + H)+.

References

[1] Patent: US2004/38855, 2004, A1
[2] Patent: WO2004/5257, 2004, A1. Location in patent: Page 54
[3] Patent: US6727264, 2004, B1. Location in patent: Page column 56; 91
[4] Patent: US2005/154020, 2005, A1. Location in patent: Page/Page column 8
[5] Patent: US2005/154022, 2005, A1. Location in patent: Page/Page column 4; 9

4-(3-AMINO-PHENYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(387827-19-2)Related Product Information

• tert-butyl 4-(3-cyano-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate
• TERT-BUTYL 4-BROMOBENZYLCARBAMATE
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• tert-butyl 4-(2-aminoethyl)-3,3-difluoropiperidine-1-carboxylate
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• INDEX NAME NOT YET ASSIGNED
• tert-butyl 4-(2-bromo-5-fluoropyridin-4-yl)-4-hydroxypiperidine-1-carboxylate
• 5H-Pyrrolo[3,2-c]pyridine-5-carboxylic acid, 1,4,6,7-tetrahydro-4-oxo-2-(4-pyridinyl)-, 1,1-dimethylethyl ester
• 1-Piperazinecarboxylic acid, 4-[3-bromo-4-(methoxycarbonyl)phenyl]-, 1,1-dimethylethyl ester
• 1-Boc-4-(2-hydroxyethyl)piperidine
• 4-(2-AMINO-PHENYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 4-(3-AMINO-PHENYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER