[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:12]2[CH:13]=[N:14][CH:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.[C-:16]#[N:17].[K+].C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>C(#N)C>[ClH:1].[ClH:1].[C:16]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:12]2[CH:13]=[N:14][CH:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1)#[N:17]A solution of 37 g of 5-(5-chloropentyl)-imidazo[1,5-a]pyridine, 21.7 g of potassium cyanide and 3 g of dibenzo-18-crown-6 in acetonitrile is heated under reflux for 20 hours. The acetonitrile is evaporated under reduced pressure, the residue is partitioned between water and methylene chloride, and the methylene chloride extract is evaporated to dryness. Treatment of a solution of the residue in ether with ethanolic hydrochloric acid yields 5-(5-cyanopentyl)-imidazo[1,5-a]pyridine hydrochloride melting at 178°-80°.
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