Diethyl Ether → HCID 14371619, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.0 grams(3.65 mmol) of Compound L from step B, 0.55 mL (3.65 mmol) 2-bromoacetaldehyde diethyl acetal, and 1.0 grams (7.3 mmol) anhydrous potassium carbonate in 35 mL dry DMF was stirred at 150° C. for 4 hours. After cooling to room temperature, the mixture was poured into 300 mL ether, washed with three 50 mL portions of water, dried (MgSO4) and evaporated. The residue was purified by flash chromatography, eluting with 1:1 hexane-ethyl acetate to give 1.1 grams (77%) of N-(2,2-diethoxyethyl)-trans-1-(3-methoxy-4-chlorophenyl-2-indanamine (Compound M) as an oil, 200 MHz NMR(CDCl3) d 1.15 (tr,6H,J=7 Hz), 2.70-290(m,3H), 3.20-3.70 (m,6H), 4.09 (d,1H,J=8 Hz), 4.55(tr,1H,J=5 Hz), 6.70-6.90 (m,3H), 7.10-7.30 (m,4H).

Provenance & Evidence