Potassium Cyanide → HCID 70170207, compound

HRID 70794Notes

Reaction equation

HRID 70794 reaction equation
[C-:1]#[N:2].[K+].Cl.Cl[CH2:6][C:7]1[NH:11][C:10]2[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=2[N:8]=1.C(=O)([O-])O.[Na+]>CCO>[NH:8]1[C:9]2[CH2:15][CH2:14][CH2:13][CH2:12][C:10]=2[N:11]=[C:7]1[CH2:6][C:1]#[N:2]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 13697832116269-41-1

Product 1

HCID 70170207HCID 70170207, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution (30 ml) of potassium cyanide (15 g) was ice-cooled, then, an EtOH (140 ml) solution of 2-(chloromethyl)-4,5,6,7-tetrahydro-1H-benzimidazole hydrochloride (12.0 g) was added, and stirring was performed at room temperature for 1 hour and then at 50° C. for 1, hour. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction liquid, followed by concentration under reduced pressure and extraction with chloroform. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (28% aqueous ammonia/methanol/chloroform) to obtain 4,5,6,7-tetrahydro-1H-benzimidazol-2-yl acetonitrile (8.6 g).

Workup

  1. temperaturecooled
  2. customat 50° C.
  3. concentrationfollowed by concentration under reduced pressure and extraction with chloroform
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (28% aqueous ammonia/methanol/chloroform)

Sources & evidence

ORD record
ord-5ad1a409f8ef42a49924cb83dd1a128b
Source dataset
uspto-grants-2014_09
Patent number
US08822688B2

Reaction notes

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