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

HRID 465348Notes

Reaction equation

HRID 465348 reaction equation
C(N(CC)CC)C.O.[OH:9]N1C2C=CC=CC=2N=N1.[CH:19]1([N:25]=[C:26]=[N:27][CH:28]2[CH2:33]C[CH2:31][CH2:30][CH2:29]2)CCCCC1.[NH2:34][CH:35]1[CH2:41][CH2:40][NH:39][C:37](=[O:38])[CH2:36]1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:19][N:25]1[CH:33]=[C:28]([CH:29]=[CH:30][C:31]([NH:34][CH:35]2[CH2:41][CH2:40][NH:39][C:37](=[O:38])[CH2:36]2)=[O:9])[N:27]=[CH:26]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 199802604-Aminopiperidin-2-one

Product 1

HCID 538765823-{beta-(1-Methylimidazole-4-yl)acryloyl}amino-delta-valerolactamYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of β-(1-methylimidazole-4-yl)acrylrate hydrochloride (7 g, 37.1 mmole) in dimethylformamide (60 ml) was added triethylamine (7.51 g, 74.2 mmole) and 1-hydroxybenzotriazole hydrate (6.25 g, 40.8 mmole) and the mixture was ice-cooled, and then a solution of dicyclohexylcarbodiimide (8.42 g, 40.8 mmole) in dimethylformamide (15 ml) was added dropwise. After stirring at 80° C. for 30 minutes, followed by at room temperature for 30 minutes, 3-amino-δ-valerolactam (5.08 g, 44.5 mmole) was added to the reaction mixture which was heated with stirring for 13 hours. After cooling to room temperature, a sodium bicarbonate solution was added to the mixture which was extracted with a chloroform-methanol mixed solvent. After drying over magnesium sulfate, the solvent was removed under reduced pressure. The residue was subjected to silica gel flash chromatography and then recrystallized from ethanol/chloroform to obtain the titled compound (6.72 g, 73.0%).

Workup

  1. temperaturecooled
  2. waitfollowed by at room temperature for 30 minutes
  3. temperaturewas heated
  4. stirringwith stirring for 13 hours
  5. temperatureAfter cooling to room temperature
  6. extractionwas extracted with a chloroform-methanol mixed solvent
  7. dry with materialAfter drying over magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customrecrystallized from ethanol/chloroform

Sources & evidence

ORD record
ord-cb67409c2f3945e1b3a66c44315c4520
Source dataset
uspto-grants-1992_10
Patent number
US05153201

Reaction notes

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