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TERT-BUTYL 4-(4-CYANO-2-NITROPHENYLAMINO)PIPERIDINE-1-CARBOXYLATE synthesis

2synthesis methods
1009-35-4 Synthesis
4-FLUORO-3-NITROBENZONITRILE

1009-35-4
225 suppliers
$8.00/1g

87120-72-7 Synthesis
4-Amino-1-Boc-piperidine

87120-72-7
28 suppliers
$6.00/1g

TERT-BUTYL 4-(4-CYANO-2-NITROPHENYLAMINO)PIPERIDINE-1-CARBOXYLATE

320406-05-1
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Yield:320406-05-1 100%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide at 20; for 72 h;

Steps:



Preparation of tert-butyl 4-[(4-cyano-2-nitrophenyl)amino]piperidine-1- carboxylate; tert-butyl 4-[(4-cyano-2-nitrophenyl)amino]piperidine-1-carboxylate 4-Amino-piperidine-1-carboxylic acid tert-butyl ester (6.15 g, 30.7 mmol), 4-fluoro-3- nitro-benzonitrile (5.0 g, 30 mmol), and N,N-diisoproprylethylamine (10.5 ml_, 60.2 mmol) were combined in 40 mL N,N-dimethylformamide and stirred at ambient temperature for 3 days. The reaction was then diluted with 100 mL water and 250 mL ethyl acetate. Seperated layers, washed with 0.5M aq. hydrogen chloride (3 x 100 mL), then added about 100 mL tetrahydrofuran which caused the suspended solids to dissolve. Washed with brine (2 x 100 mL), dried with magnesium sulfate, filtered and concentrated to yield title compound. (10.55 g, quant, yield) APCI" 346.1; Anal. HPLC Retention time = 19.3 minutes.

References:

WO2008/84300,2008,A1 Location in patent:Page/Page column 84-85