Potassium Cyanide → Hydrochloric Acid

HRID 2417808Notes

Reaction equation

HRID 2417808 reaction equation
[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]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 26541Dibenzo-18-crown-6HCID 204466765-(5-Chloropentyl)imidazo[1,5-a]pyridine

Product 2

HCID 313Hydrochloric AcidHCID 204466655-(5-Cyanopentyl)-imidazo[1,5-a]pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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°.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe acetonitrile is evaporated under reduced pressure
  3. customthe residue is partitioned between water and methylene chloride
  4. extractionthe methylene chloride extract
  5. customis evaporated to dryness

Sources & evidence

ORD record
ord-7bbda157222d44e89a43344261bb1458
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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