For the 65 th anniversary of Professor Keith Smith a one-time tutee of one (JAJ) of the authors -didn't he do well! Abstract Reaction of indole with the combination 1-cyclohexyl-2-pyrrolidinone and phosphoric trichloride gives the hydrochloride of 3-(1-cyclohexylpyrrolidin-2-ylidene)-3H-indole. Treatment of this with base at room temperature causes hydrolytic ring opening producing 4-(cyclohexylamino)-1-(1H-indol-3-yl)butan-1-one but careful low-temperature basification allows the isolation of 3-(1-cyclohexylpyrrolidin-2-ylidene)-3H-indole itself. The crystal structure of the hydrochloride, as a dihydrate, was determined.
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