Triethylamine → 3-{beta-(1-Ethyl-2-phenylimidazole-4-yl)acryloyl}amino-delta-valerolactam

HRID 465349Notes

Reaction equation

HRID 465349 reaction equation
Cl.[CH2:2]([N:4]1[CH:8]=[C:7]([CH:9]=[CH:10][C:11]([OH:13])=O)[N:6]=[C:5]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:3].C(N(CC)CC)C.[NH2:27][CH:28]1[CH2:34][CH2:33][NH:32][C:30](=[O:31])[CH2:29]1.C(=O)(O)[O-].[Na+]>S(Cl)(Cl)=O.O1CCCC1>[CH2:2]([N:4]1[CH:8]=[C:7]([CH:9]=[CH:10][C:11]([NH:27][CH:28]2[CH2:34][CH2:33][NH:32][C:30](=[O:31])[CH2:29]2)=[O:13])[N:6]=[C:5]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 199802604-Aminopiperidin-2-oneHCID 70344434beta-(1-Ethyl-2-phenylimidazole-4-yl)acrylate hydrochloride

Product 1

HCID 545002753-{beta-(1-Ethyl-2-phenylimidazole-4-yl)acryloyl}amino-delta-valerolactamYield 422.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent2×

Procedure

β-(1-Ethyl-2-phenylimidazole-4-yl)acrylate hydrochloride (5.49 g, 20.3 mmole) was heated with stirring in thionyl chloride (50 ml) for 50 minutes. After excessive thionyl chloride was completely distilled off under reduced pressure, tetrahydrofuran (50 ml) and triethylamine (4.12 g, 40.7 mmole) were added and then 3-amino-δ-valerolactam (2.79 g, 24.4 mmole) was added to the mixture with cooling, followed by stirring at room temperature overnight. A sodium bicarbonate solution was added to the reaction mixture which was extracted with a chlorofolm-methanol mixed solvent. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel flash chromatography to obtain the titled compound (29 g, 62.3%).

Workup

  1. additionwere added
  2. temperaturewith cooling
  3. extractionwas extracted with a chlorofolm-methanol mixed solvent
  4. dry with materialAfter drying over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9afc9657b35444d38a2628ef6d566be9
Source dataset
uspto-grants-1992_10
Patent number
US05153201

Reaction notes

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