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ChemicalBook CAS DataBase List 1-(4-TERT-BUTYLPHENYL)PIPERAZINE
68104-61-0

1-(4-TERT-BUTYLPHENYL)PIPERAZINE synthesis

3synthesis methods
-

Yield:68104-61-0 48.2%

Reaction Conditions:

with sodium t-butanolate;dichlorobis(tri-O-tolylphosphine)palladium in toluene at 100; for 3 h;

Steps:

10

Reference Example 10 1-(4-t-butylphenyl)piperazine 1-Bromo-4-t-butylbenzene (2.38 mL, 14 mmol), piperazine (1.8 g, 21 mmol), sodium t-butoxide (1.95 g, 20.3 mmol) and dichlorobis(tri-o-tolylphosphine)palladium(II) (330.1 mg, 0.42 mmol) were dissolved in anhydrous toluene and reacted for 3 hours while heating at 100° C. After identifying complete disappearance of 1-bromo-4-t-butylbenzene by TLC, the reaction solution was filtered with celite. The filtrate was concentrated and purified by separation through column chromatography (CH2Cl2/MeOH, 1:1). A target compound (1.47 g, 6.732 mmol, 48.2%) was yielded. 1H NMR (CDCl3, 300 MHz) δ 7.31 (d, J=8.6 Hz, 2H), 6.90 (d, J=8.6 Hz, 2H), 3.14 (br, 4H), 3.04 (br, 4H), 1.57 (s, 1H, NH), 1.31 (s, 9H). 13C NMR (CDCl3, 75 MHz) δ 149.5, 142.4, 125.8, 115.7, 50.6, 46.3, 33.9, 31.4.

References:

US2011/319619,2011,A1 Location in patent:Page/Page column 6

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