The introduction of 1-Boc-piperazine

A applied and scalable alertness of 1-(7-fluoronaphthalen-1-yl)-piperazine hydrochloride is reported. The aboriginal avenue for the amalgam of this admixture complex the use of 1-amino-7-fluoronaphthalene and bis(2-chloroethyl)amine hydrochloride, two awful baneful compounds. A new agreement has been developed that employs a palladium-catalyzed Buchwald-Hartwig cross-coupling acknowledgment amid 1-Boc-piperazine and 1-bromo-7-fluoronaphthalene followed by piperazine deprotection with HCl gas. In addition, an able aegis abatement agreement accustomed for the alertness of the ambition atom with beneath than 20 ppm of this metal. This alignment has been auspiciously implemented to aftermath multigram quantities of 1 with accomplished abstention and low aegis content.The reactions of the electron donor tert-Butyl piperazine -1-carboxylate (1-Boc- PIP) with the π-acceptors 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and 2,3,5,6-tetrachloro-1,4-benzoquinone (CHL) and the σ- acceptor iodine were advised spectrophotometrically in chloroform at 25 °C. The bittersweet and cyberbanking spectra of the produced charge-transfer complexes were recorded, in accession to thermal analysis. The formed CT-complexes accept the formulas of [(1-Boc PIP)2 I] I3, [(1-Boc PIP)(DDQ)] and [(1-Boc PIP)(CHL)].
-(4-Vinyl-phenyl)-piperazine-1-carboxylic acerbic tert-butyl ester (4): A admixture of 4-bromostyrene (1.0 g, 5.46 mmol), 1-Boc-piperazine (1.32 g, 7.10 mmol), sodium ter-butoxide (0.78 g, 8.19 mmol) and PdCl2[P(oTol)3]2 (0.12 g, 0.16 mmol) was acrimonious in anhydrous toluene (20 mL) at 100 °C beneath argon for 3 h. The acknowledgment admixture was again concentrated beneath bargain burden and subjected to beam cavalcade chromatography to accord 4 (0.91 g) in 58% yield. 1H NMR (500 MHz, CDCl3): δ 1.51 (9H, s), 3.18 (4H, s), 3.61 (4H, s), 5.13 (1H, d, J = 10.7 Hz), 5.63 (1H, d, J = 17.5 Hz), 6.67 (1H, dd, J = 10.9, 17.5 Hz), 6.88 – 6.95 (2H, ample doublet), 7.36 (2H, d, J = 8.7 Hz); ESI MS: 311.8 (M+23).
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