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

HRID 568550Notes

Reaction equation

HRID 568550 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-14d0881d2b4146e39a6900b32fe9153e
Source dataset
uspto-grants-1988_03
Patent number
US04728645

Reaction notes

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