4-(4-Aminophenyl)piperazine-1-carboxylic acid tert-butyl ester Chemical Properties

Boiling point:

441.1±40.0 °C(Predicted)

Density 

1.145±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

7.69±0.10(Predicted)

form 

Solid

Appearance

Brown to reddish brown Solid

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C15H23N3O2/c1-15(2,3)20-14(19)18-10-8-17(9-11-18)13-6-4-12(16)5-7-13/h4-7H,8-11,16H2,1-3H3

InChIKey

RXFHRKPNLPBDGE-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCN(C2=CC=C(N)C=C2)CC1

Safety Information

HS Code 

2921420090

4-(4-Aminophenyl)piperazine-1-carboxylic acid tert-butyl ester Usage And Synthesis

Uses

1-Boc-4-(4-aminophenyl)piperazine is a important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff.

Synthesis

The general procedure for the synthesis of tert-butyl 4-(4-aminophenyl)piperazine-1-carboxylate from tert-butyl 4-(4-nitrophenyl)piperazine-1-carboxylate was as follows: first, tert-butyl 4-(4-nitrophenyl)piperazine-1-carboxylate (8.2 g, 26.68 mmol) was dissolved in methanol (100 mL), followed by purging with nitrogen and depressurization. Next, 10% wet palladium carbon catalyst was added to the solution and the hydrogenation reaction was carried out under hydrogen pressure of 50 psi for 16 hours. Upon completion of the reaction, the mixture was filtered through diatomaceous earth to remove the catalyst, and the filtrate was subsequently concentrated under reduced pressure to afford tert-butyl 4-(4-aminophenyl)piperazine-1-carboxylate (7.4 g, 97% yield) as a dark blue oily product, which was used directly in subsequent reactions without further purification. The molecular formula of the product was C15H23N3O2, and the mass spectrometry analysis showed that the m/z was 277.9 (M + H).

References

[1] Patent: WO2006/38039, 2006, A1. Location in patent: Page/Page column 17; 30
[2] Patent: EP1215208, 2002, A2. Location in patent: Example C(101)
[3] Patent: WO2012/110773, 2012, A1. Location in patent: Page/Page column 52; 53
[4] Patent: WO2014/26242, 2014, A1. Location in patent: Page/Page column 77
[5] Patent: WO2014/27199, 2014, A1. Location in patent: Page/Page column 55

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