Tris(1,1-dimethylethyl)phosphine → 4-(4-Benzyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

To a solution of 1-Boc-piperazine (2.5 g, 13.1 mmol) and 4-iododiphenylmethane (4.0 g, 13.1 mmol) in toluene were added the following reagents: Pd2(dba)3 (0.36 g, 0.3 mmol), PtBu3 (0.7 g 3.0 mmol) and NaO-t-Bu (1.26 g, 13.1 mmol). The reaction mixture was stirred at ambient temperature overnight and then filtered. The filtrate was purified using silica gel chromatography (1% MeOH in CH2Cl2) to yield the title compound as a light tan oil (4.6 g, 99%): MS (ESI) m/z 353 (M+H); 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 3.08 (t, J=5.2 Hz, 4H), 3.56 (s, J=5.2 Hz, 4H), 3.91 (s, 2H), 6.85 (dd, J=2, 6.8 Hz, 2H), 7.09 (dd, J=2, 6.4 Hz, 2H), 7.16-7.19 (m, 3H), 7.25-7.29 (m, 2H).

Provenance & Evidence