Sodium Hydroxide → (1S)-8-Chloro-9-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

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Reaction Conditions

Reaction Steps

A solution of (S)-N-trifluoroacetyl-8-chloro-9-fluoro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (160 mg, 0.22 mmol) in methanol (3 mL) was treated with 15% aqueous NaOH (2 mL), and stirred for 3.5 hours at 25° C. The product mixture was concentrated, extracted 3 times with CH2Cl2 (5 mL), dried with Na2SO4 and concentrated to give 93 mg of a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.06 (dd, J=8, 8 Hz, 1H), 6.75 (d, J=8 Hz, 1H), 3.58 (m, 1H), 3.25-3.15 (m, 3H), 2.93 (d, J=13 Hz, 1H) 2.75-2.60 (m, 3H), 1.96 (bs, 1H), 1.33 (d, J=8 Hz, 3H). MS calculated for C11H13ClFN+H: 214, observed: 214.

Provenance & Evidence