Triethylamine → 2-(3,4-Dimethoxy-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester

HRID 1094986Notes

Reaction equation

HRID 1094986 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[NH2:17])[CH3:2].C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[C:31](Cl)=[O:32]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[NH:17][C:31](=[O:32])[C:30]1[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:28]([O:27][CH3:26])[CH:29]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77070Veratroyl chloride2×HCID 613065672-Amino-5-piperidin-1-yl-benzoic acid ethyl ester2×

Product 1

HCID 666378362-(3,4-Dimethoxy-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Subsequently, crude 2-amino-5-piperidin-1-yl-benzoic acid ethyl ester (compound A) (1.3 g) was dissolved in anhydrous methylene chloride (100 ml). Triethylamine (5.6 ml) and 3,4-dimethoxy-benzoyl chloride (compound B) (1.8 g) were added at 0° C., and the mixture was stirred at room temperature for 24 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-chloroform system to give 2-(3,4-dimethoxy-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester (960 mg, yield 52%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated under the reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluted with a hexane-chloroform system

Sources & evidence

ORD record
ord-8d334f2f743741cd838ea241e13d709d
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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