ChemicalBook CAS DataBase List 4-(4-Boc-piperazin-1-yl)-3-chloroaniline

4-(4-Boc-piperazin-1-yl)-3-chloroaniline synthesis

5synthesis methods

Product Name:4-(4-Boc-piperazin-1-yl)-3-chloroaniline
CAS Number:193902-81-7
Molecular formula:C15H22ClN3O2
Molecular Weight:311.81

193902-80-6 Synthesis

1-Boc-4-(2-chloro-4-nitrophenyl)piperazine

193902-80-6
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4-(4-Boc-piperazin-1-yl)-3-chloroaniline

193902-81-7
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Yield:193902-81-7 73%

Reaction Conditions:

Stage #1: tert-butyl 4-(2-chloro-4-nitro-phenyl)piperazine-1-carboxylatewith acetic acid;zinc in tetrahydrofuran;methanol at 20; for 1 h;
Stage #2: with sodium hydrogencarbonate in tetrahydrofuran;methanol;water; for 1 h;

Steps:

221.221b

Zinc powder (1.96 g) and acetic acid (1.0 mL) were added slowly to a solution of 4-(2-chloro-4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (1.02 g) obtained in Example (221 a) in methanol (20 mL) and anhydrous tetrahydrofuran (20 mL) at room temperature. The reaction mixture was stirred for one hour, followed by addition of a saturated sodium hydrogen carbonate aqueous solution. The mixture was stirred for another hour and filtered through Celite, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate and concentrated. The residue was purified by column chromatography (dichloromethane:ethyl acetate 4:1). The obtained solid was vigorously stirred in hexane/isopropanol (5:1), collected by filtration and dried under reduced pressure, and 684 mg (73%) of the title compound was obtained as a pale yellow solid. ¹H NMR(400MHz,CDCl₃):δ(ppm)=6.86(1H, d, J=8.6Hz), 6.61(1H, d, J=2.8Hz), 6.46(1H, dd, J=8.6 and 2.8Hz), 5.06(2H, s), 3.41(4H, t, J=4.9Hz), 2.73(4H, t, J=4.9Hz), 1.41(9H, s).

References:

EP1764360,2007,A1 Location in patent:Page/Page column 161

350-30-1 Synthesis