Hydrochloric Acid → HCID 14097213, compound

HRID 568559Notes

Reaction equation

HRID 568559 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[C:12]([CH2:13][CH2:14][CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].CC(C)([O-])C.[K+].Cl>O1CCCC1>[C:1]([C:3]1[CH:23]=[CH:22][C:6]([CH:7]2[N:8]3[CH:9]=[N:10][CH:11]=[C:12]3[CH2:13][CH2:14][CH:15]2[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 23665647Potassium tert-butoxideHCID 57286186HCID 57286186, compound

Product 1

HCID 14097213HCID 14097213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.27 g of ethyl 5-[1-(4-cyanobenzyl)imidazol-5-yl)-1-pent-2-enoate in 27 ml of tetrahydrofuran at 5° under nitrogen is treated with 0.52 g of potassium tert-butoxide. The reaction mixture is stirred at 5° for 2 h and 10 ml of 1N hydrochloric acid is added. The layers are separated. The organic phase is extracted with 1N hydrochloric acid (2×10 ml). The combined aqueous layers are extracted with ether, adjusted to pH=8 and extracted with methylene chloride (3×15 ml). The organic phase is dried and evaporated to yield the product which is treated with one molar equivalent of ethereal hydrogen chloride. The resulting solid is recrystallized from acetone to yield 5-(4-cyanophenyl)-6-ethoxycarbonylmethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine, m.p. 126°-127°.

Workup

  1. customThe layers are separated
  2. extractionThe organic phase is extracted with 1N hydrochloric acid (2×10 ml)
  3. extractionThe combined aqueous layers are extracted with ether
  4. extractionextracted with methylene chloride (3×15 ml)
  5. customThe organic phase is dried
  6. customevaporated
  7. customto yield the product which
  8. customThe resulting solid is recrystallized from acetone

Sources & evidence

ORD record
ord-b8948a4f77444734a6bfeb5b33778919
Source dataset
uspto-grants-1988_03
Patent number
US04728645

Reaction notes

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