Pyridine → 2-(3-Chloromethyl-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester

HRID 1094989Notes

Reaction equation

HRID 1094989 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].N1C=CC=CC=1.CO[C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1OC)[C:30](Cl)=[O:31].[CH2:38]([Cl:40])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:30](=[O:31])[C:29]1[CH:33]=[CH:34][CH:35]=[C:27]([CH2:38][Cl:40])[CH:28]=1)[CH3:2]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 77070Veratroyl chloride2×HCID 613065672-Amino-5-piperidin-1-yl-benzoic acid ethyl ester2×

Product 1

HCID 666387082-(3-Chloromethyl-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester

Procedure

2-Amino-5-piperidin-1-yl-benzoic acid ethyl ester (compound A) (1.6 g) synthesized by the above process was dissolved in anhydrous methylene chloride (20 ml). Pyridine (1.0 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (1.2 ml) were added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for one hr. After the completion of the reaction, the reaction solution was concentrated under the reduced pressure. Distilled water was added to the residue, and the mixture was subjected to separatory extraction with ethyl acetate. The organic layer was dried over sodium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-chloromethyl-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester as a useful intermediate (1.7 g, yield 63%).

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction solution was concentrated under the reduced pressure
  3. additionDistilled water was added to the residue
  4. extractionthe mixture was subjected to separatory extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationwas then concentrated under the reduced pressure
  7. customThe residue was purified by column chromatography
  8. washeluted with a chloroform-methanol system

Sources & evidence

ORD record
ord-c583d57d53404ff5a869e4eadd04a455
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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