Hydrochloric Acid → HCID 136364245, compound

Participants

Reaction Conditions

Reaction Steps

NaNO2 (0.27 g, 4.30 mmol) was added to a mixture of hydrochloric acid (0.64 mL, 7.70 mmol, conc.) and p-methylaniline (0.41 g, 3.80 mmol) in ice-water (20 mL). The mixture was stirred at 0° C. for 10 min. and then added to an ice-cold solution of (R)-N,N-diisopropyl-3-(2-hydroxyphenyl)-3-phenylpropanamine (1.00 g, 3.21 mmol) in THF (3 mL), H2O (12 mL) and sodium hydroxide (0.69 g, 17.32 mmol). After stirring the mixture for 20 minutes, it was extracted with toluene, dried (MgSO4), and evaporated to give an oil, which was chromatographed on (toluene-ethyl acetate-triethylamine 8:1:1) to give 0.83 g, 1.93 mmol, (60%) of the title compound. 1H NMR (CDCl3) δ1.12 (d, 6H), 1.19 (d, 6H), 2.22 (m, 1H), 2.43 (m, 5H), 2.79 (m, 1H), 3.32 (m, 2H), 4.57 (d, 1H), 6.98 (d, 1H), 7.24 (m, 3H), 7.36 (m, 4H), 7.66 (m, 4H).

Provenance & Evidence