4-(4-Boc-piperazin-1-yl)-3-fluoroaniline Chemical Properties

Boiling point:

439.6±45.0 °C(Predicted)

Density 

1.198±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

solid

pka

6.67±0.10(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C15H22FN3O2/c1-15(2,3)21-14(20)19-8-6-18(7-9-19)13-5-4-11(17)10-12(13)16/h4-5,10H,6-9,17H2,1-3H3

InChIKey

IULXQAJBODFBAK-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCN(C2=CC=C(N)C=C2F)CC1

Safety Information

HS Code 

2933599590

4-(4-Boc-piperazin-1-yl)-3-fluoroaniline Usage And Synthesis

Synthesis

Preparation of 3-4-2: [3-Fluoro-4-(Boc-piperazinyl)]aniline To 150 mL of ethyl acetate were sequentially added 9.3 g (28.6 mmol) of tert-butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate synthesized by the preparation of Example 3-4-1 and 930 mg (10 wt%) of Pd/C catalyst. The mixture was placed in a hydrogen reactor and reacted at 4 bar hydrogen pressure for 6 hours. Upon completion of the reaction, the Pd/C catalyst was removed by filtration. The filtrate was concentrated by distillation under reduced pressure and subsequently dried under vacuum at about 40 °C to give 8.22 g (yield: 97%) of the title compound. Mass spectrum (M + H)+: 296.11 1H-NMR (DMSO-d6) δ: 1.42 (s, 9H), 2.76 (br m, 4H), 3.43 (br m, 4H), 5.02 (s, 2H), 6.33 (m, 2H), 6.79 (m, 1H).

References

[1] Patent: US2011/306606, 2011, A1. Location in patent: Page/Page column 15
[2] Patent: EP2394993, 2011, A2. Location in patent: Page/Page column 23
[3] Patent: WO2005/82892, 2005, A2. Location in patent: Page/Page column 62-63
[4] Patent: WO2004/18439, 2004, A1. Location in patent: Page 31
[5] Patent: US2007/100141, 2007, A1. Location in patent: Page/Page column 27

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