Acetic Acid → 5-(p-Cyanophenyl)-5-ethoxycarbonyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 477996Notes

Reaction equation

HRID 477996 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[N:9]([CH:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[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>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:10]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[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 199304165-(3-chloropropyl)-1-(alpha-ethoxycarbonyl-p-cyanobenzyl)-1H-imidazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 152947195-(p-Cyanophenyl)-5-ethoxycarbonyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.1 g of 5-(3-chloropropyl)-1-(α-ethoxycarbonyl-p-cyanobenzyl)-1H-imidazole in 50 ml of tetrahydrofuran is cooled to 0° in an ice bath. To this is added 8.0 g of potassium-t-butoxide as a solid in portions. The mixture is stirred at room temperature for 2 h, 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. The solid is collected to yield 5-(p-cyanophenyl)-5-ethoxycarbonyl-5,6,7,8-tetrahydroimidazo[1,5-a]-pyridine.

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. customThe solid is collected

Sources & evidence

ORD record
ord-3263881fe7384e19b75c43256ae48994
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

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