2,3-Dimethoxycinnamic acid → 3-(2,3-Dimethoxycinnamoyl)amino-delta-valerolactam

HRID 465347Notes

Reaction equation

HRID 465347 reaction equation
[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:4]=1[CH:5]=[CH:6][C:7]([OH:9])=O.[NH2:16][CH:17]1[CH2:23][CH2:22][NH:21][C:19](=[O:20])[CH2:18]1>O1CCCC1.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:4]=1[CH:5]=[CH:6][C:7]([NH:16][CH:17]1[CH2:23][CH2:22][NH:21][C:19](=[O:20])[CH2:18]1)=[O:9]

Participants

5

Reactant 2

HCID 995252,3-Dimethoxycinnamic acidHCID 199802604-Aminopiperidin-2-one

Product 1

HCID 536980503-(2,3-Dimethoxycinnamoyl)amino-delta-valerolactamYield 39.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dimethoxycinnamic acid (5.0 g) in tetrahydrofuran (50 ml) was added N,N'-carbonyldiimidazole (4.28 g) and the mixture was stirred at room temperature for 30 minutes. To this was added 3-amino-δ-valerolactam (3.02 g), followed by stirring overnight. The reaction solution was diluted with chloroform and washed with a saturated soldium bicarbonate solution and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was chromatographed on a silica gel column to obtain the titled compound (2.91 g, 39.8%).

Workup

  1. stirringby stirring overnight
  2. washwashed with a saturated soldium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-c66ccc99381b479bb5bf7c8f95d8037c
Source dataset
uspto-grants-1992_10
Patent number
US05153201

Reaction notes

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