Hydrochloric Acid → 2,4-Dichloro-N-{[1-(cyclopropylmethyl)-4-oxocyclohexyl]methyl}benzamide

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Reaction Steps

2,4-Dichloro-N-[(8-cyclopropylmethyl-1,4-dioxaspiro[4.5]dec-8-yl)methyl]benzamide (11 g; 27.6158 mmol) was dissolved in THF (80 ml) and HCl (2M; 80 ml) and the solution stirred at ambient temperature for 18 hours. The solution was adjusted to pH 9 with 10N NaOH solution and extracted with DCM (2×75 ml). The combined organics were dried (MgSO4) filtered and evaporated to give an oil which was crystallised from EtOAc isohexane as a white solid (8.0 g) 1H NMR δ (ppm) (CDCl3): 7.67 (1 H, d, J=8.3 Hz), 7.44 (1 H, d, J=2.0 Hz), 7.34 (1 H, dd, J=2.0, 8.3 Hz), 6.37 (1 H, s), 3.72 (2 H, d, J=6.4 Hz), 2.57-2.49 (2 H, m), 2.39-2.31 (2 H, m), 1.92-1.80 (4 H, m), 1.43 (2 H, s), 0.77-0.69 (1 H, m), 0.58-0.54 (2 H, m), 0.11 (2 H, q, J=5.0 Hz). MS (m/e)=354.

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