Pyridine → HCID 66638508, compound

HRID 1095010Notes

Reaction equation

HRID 1095010 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:7]=[CH:6][C:5]=1[NH2:20].N1C=CC=CC=1.[Cl:28][CH2:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](O)=[O:34]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:7]=[CH:6][C:5]=1[NH:20][C:33](=[O:34])[C:32]1[CH:36]=[CH:37][CH:38]=[C:30]([CH2:29][Cl:28])[CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2417523-(Chloromethyl)benzoic acid2×HCID 66638605HCID 66638605, compound2×

Product 1

HCID 66638508HCID 66638508, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (compound A) (1.1 g) produced by the above process was dissolved in anhydrous methylene chloride (12 ml). Pyridine (600 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (600 μl) were added dropwise to the solution at 0° C., and the mixture was stirred at room temperature for one hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then 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 chloroform-methanol system to give 2-(3-chloromethyl-benzoylamino)-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (1.5 g, yield 93%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was then 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 chloroform-methanol system

Sources & evidence

ORD record
ord-659d9536bb1c4f97bc1b46ab573aaee6
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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