ChemicalBook CAS DataBase List 1-(9H-FLUOREN-9-YL)PIPERAZINE

1-(9H-FLUOREN-9-YL)PIPERAZINE synthesis

5synthesis methods

Product Name:1-(9H-FLUOREN-9-YL)PIPERAZINE
CAS Number:129604-54-2
Molecular formula:C17H18N2
Molecular Weight:250.34

110-85-0 Synthesis

110-85-0
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1940-57-4
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129604-54-2
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$203.00/100mg

Yield:129604-54-2 100%

Reaction Conditions:

with triethylamine in tetrahydrofuran; for 6 h;Reflux;Inert atmosphere;

Steps:

2.1 4.2.1. 1-(9H-Fluoren-9-yl)piperazine (3)

A solution of 9-bromofluorene 2 (8.2 mmol, 2.0 g, 1.0 eq), triethylamine (1.2 mmol, 165 μL, 0.15 eq) and piperazine (61.1 mmol, 5.27 g, 7 eq) in dry THF (50.0 mL) was refluxed under argon for 6 h.
The reaction mixture was then filtered off and the filtrate was concentrated under vacuum pressure.
The resulting crude product was purified by flash chromatography (isocratic 95/5 dichloromethane/methanol) to afford a white powder (2.04 g, 100%). TLC R_f: 0.12 (dichloromethane/methanol 97/3); mp: 133.6 °C; IR (cm^-1): 738, 805, 1007, 1138, 1325, 1448, 2831, 2940, 3294. ¹H NMR (300 MHz, DMSO-d6) δ (ppm): 2.46 (m, 4H); 2.66 (m, 4H); 4.86 (s, 1H); 7.32 (td, J = 1.5 Hz, 3.5 Hz, 2H); 7.40 (t, J = 7.5 Hz, 2H); 7.63 (d, J = 7.2 Hz, 2H), 7.83 (d, J = 7.5 Hz, 2H).
¹³C NMR (75 MHz, DMSO-d6) δ (ppm): 46.7 (2 * CH₂), 50.4 (2 * CH₂), 70.2 (CH), 120.4 (2 * CH), 126.3 (2 * CH), 127.5 (2 * CH), 128.5 (2 * CH), 140.9 (2 * C), 144.4 (2 * C). MS (ESI) m/z: 251.3 [M+H⁺]. HRMS (ESI): for C₁₇H₁₉N₂ [M+H⁺]: calcd: 251.1551; found: 251.1548.

References:

Chollet, Aurélien;Mori, Giorgia;Menendez, Christophe;Rodriguez, Frédéric;Fabing, Isabelle;Pasca, Maria Rosalia;Madacki, Jan;Korduláková, Jana;Constant, Patricia;Quémard, Anna?k;Bernardes-Génisson, Vania;Lherbet, Christian;Baltas, Michel [European Journal of Medicinal Chemistry,2015,vol. 101,p. 218 - 235]