Sodium Hydroxide → (+/-)-trans-2-Pyrrolidino-6-propyl-5,5a, 6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline

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Reaction Conditions

Reaction Steps

A mixture of (±)-trans-2-chloro-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline hydrochloride (2.50 g, 8.3 mmol) and pyrrolidine hydrochloride (10 g) was heated to 210° C. to form a homogeneous molten semi-solid. After 45 minutes the molten semi-solid was poured into water, made basic with dilute NaOH solution, and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give the crude product as a brown solid. Purification by flash chromatography (10% methanol in methylene chloride, NH4OH) provided (±)-trans-2-pyrrolidino-6-propyl-5,5a, 6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline (Rf=0.45, 1.32 g, 53% yield) as a brown oil. NMR (90 MHz, CDCl3): 7.03 (doublet, J=8 Hz, 1H), 6.07 (doublet, J=8 Hz, 1H), 3.55-3.11 (multiplet, 4H), 3.11-1.00 (multiplet, 20H), 0.89 (triplet, J=7 Hz, 3H).

Provenance & Evidence