1-Indanone → 1-(1H-Inden-3-yl)pyrrolidine

Participants

Reaction Steps

According to a modification of the procedure of Noland et al (Noland, W. E.; Kaneswaran, V. J. Org. Chem. 1981, 46, 1940-1944.), 1-indanone (25.0 g, 0.189 mol) and 50 mL of pyrrolidine which had been dried over 3A sieves were added to a 500 mL, 3-neck flask equipped with an overhead stirrer, Dean-Stark apparatus and condenser which was maintained under a dry N2 atmosphere. Benzene (200 mL dried over 4A sieves) was added and the solution was brought to reflux for 30 hours. At the end of this period 1H NMR analysis of a reaction aliquot indicated a 93:7 mole percent ratio of desired product to starting material. The bulk of the solvent was removed in vacuo and the crude dark product was distilled (6″ Vigreaux column) to give pure enamine as a light yellow oil (24.3 g, 0.132 mol) in 70 percent yield. This compound was both air and water sensitive and was transferred to the dry box upon distillation. Capillary GC analysis indicated a hexane solution of distillate to be of 99 area percent purity: bp=125-127° C. @ 2.0 mm, bp. lit=118-120° C. @ 1 mm;

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