Hydrochloric Acid → 2-[4-(1-Aminoethyl)phenyl]-2-ethylbutanenitrile

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Reaction Conditions

Reaction Steps

4-(1-Cyano-1-ethylpropyl)benzonitrile (936 mg, 5.51 mmol) is added to THF (20.0 mL), and the resulting solution is cooled to −78° C. MeLi (3.44 mL, 5.51 mmol) is added, and the solution is stirred for 20 minutes. NaBH4 (208 mg, 5.51 mmol) is mixed in MeOH (20.0 mL) and added to the first solution. The resulting solution is warmed to room temperature and stirred for 1 hour. 1N HCl (50.0 mL) is added followed by 1N NaOH (60.0 mL). The aqueous phase is extracted with EtOAc (4 times 50.0 mL) and the combined organic phases are dried with MgSO4, filtered and concentrated on the rotovaporator. The product is purified by HPLC: Gilson prep pumps, Flow rate: 30 ml/min, Column: Gemini (5u) 21.2×50 mm, Mobile phase: A=water (10 mM NH4CO3) B=MeCN, (528 mg, 2.44 mmol, 44%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.77 (t, J=7.32 Hz, 6H) 1.22 (d, J=6.45 Hz, 3H) 1.82-2.07 (m, 4H) 3.97 (q, J=6.64 Hz, 1H) 7.32 (d, J=8.40 Hz, 2H) 7.40 (d, J=8.20 Hz, 2H).

Provenance & Evidence