Acetic Acid → Benzonitrile, 4-(5,6,7,8-tetrahydroimidazo(1,5-a)pyridin-5-yl)-, hydrochloride (1:1)

HRID 2290560Notes

Reaction equation

HRID 2290560 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[CH:8]=[N:7][CH:6]=1.CC(C)([O-])C.[K+].C(O)(=O)C>O1CCCC1.CC(C)=O.Cl>[ClH:1].[C:17]([C:14]1[CH:15]=[CH:16][C:11]([CH:10]2[N:9]3[CH:8]=[N:7][CH:6]=[C:5]3[CH2:4][CH2:3][CH2:2]2)=[CH:12][CH:13]=1)#[N:18]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 136882095-(3-chloropropyl) 1-(p-cyanophenylmethyl)-1H-imidazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 59694Benzonitrile, 4-(5,6,7,8-tetrahydroimidazo(1,5-a)pyridin-5-yl)-, hydrochloride (1:1)

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.1 g of 5-(3-chloropropyl)-1-p-cyanophenylmethyl-1H-imidazole in 50 ml of tetrahydrofuran is cooled to 0°. To this is added 7.0 g of potassium t-butoxide as a solid in portions. The mixture is stirred at room temperature for 2 hours, neutralized with 10% acetic acid and partitioned between methylene chloride and water. The organic layer is washed with water, dried over magnesium sulfate and evaporated to yield an oil which is dissolved in a small volume of acetone and neutralized with ethereal hydrogen chloride. On cooling, the title compound is obtained as a white solid. M.P. 201°-203°.

Workup

  1. custompartitioned between methylene chloride and water
  2. washThe organic layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto yield an oil which
  6. temperatureOn cooling

Sources & evidence

ORD record
ord-2ab0c9ba088c485f8ec93b2c5fa4f88f
Source dataset
uspto-grants-1986_10
Patent number
US04617307

Reaction notes

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