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

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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

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