Sodium Hydroxide → HCID 59807134, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1 M LiAlH4 in THF (1.82 mL, 1.82 mmol) was cooled to 0° C. then treated with 7-amino-1-(2-(dimethylamino)ethyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (225 mg, 0.91 mmol) (see experimental procedure for the synthesis of Example 25) in 10 mL THF dropwise. The suspension was stirred at room temperature overnight. After this time, the mixture was cooled to 0° C. and treated with 1 mL 1N NaOH dropwise with rapid stirring. After stirring for 20 minutes, the suspension was treated with Na2SO4. The suspension was filtered and the solid was rinsed with 50 mL 10% 2M NH3 in MeOH/CH2Cl2. The filtrate was concentrated and the dark residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a dark viscous oil (75 mg, 35.4%). 1H-NMR (CDCl3) δ 6.80-6.78 (m, 1H), 6.52-6.48 (m, 2H), 3.40 (brs, 2H), 3.21-3.17 (m, 2H), 2.87-2.83 (m, 2H), 2.70-2.66 (m, 2H), 2.47-2.43 (m, 2H), 2.27 (s, 6H), 1.72-1.64 (m, 2H), 1.59-1.55 (m, 2H). MS (EI): 234.2 (M+1).

Provenance & Evidence