Potassium Cyanide → 5-(4-Cyanobutyl)-imidazo[1,5-a]pyridine

HRID 2417831Notes

Reaction equation

HRID 2417831 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:11]2[CH:12]=[N:13][CH:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.[C-:15]#[N:16].[K+].C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>C(#N)C>[C:15]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:11]2[CH:12]=[N:13][CH:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)#[N:16]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 26541Dibenzo-18-crown-6HCID 133736305-(4-Chlorobutyl)imidazo[1,5-a]pyridine

Product 1

HCID 132061415-(4-Cyanobutyl)-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(4-chlorobutyl)imidazo[1,5-a]pyridine (5.73 g), potassium cyanide (7.18 g) and 1.0 g of dibenzo-18-crown-6 in 190 ml of acetonitrile is heated at reflux for 18 hours, cooled and evaporated to a residual oil which is partitioned between water and methylene chloride. The organic phase is dried over sodium sulfate and evaporated. The resulting solid is dissolved in ethyl acetate and filtered through 60.0 g of silica gel to yield 5-(4-cyanobutyl)-imidazo[1,5-a]pyridine m.p. 72°-75°.

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. customevaporated to a residual oil which
  4. customis partitioned between water and methylene chloride
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customevaporated
  7. dissolutionThe resulting solid is dissolved in ethyl acetate
  8. filtrationfiltered through 60.0 g of silica gel

Sources & evidence

ORD record
ord-de3d385fb8a14931ae07c9b89562f4b0
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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