Pyridine → 2-(3-Chloromethyl-benzoylamino)-5-piperidin-1-yl-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[NH2:16].N1C=CC=CC=1.CO[C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1OC)[C:29](Cl)=[O:30].[CH2:37]([Cl:39])Cl>>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[NH:16][C:29](=[O:30])[C:28]1[CH:32]=[CH:33][CH:34]=[C:26]([CH2:37][Cl:39])[CH:27]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
2-Amino-5-piperidin-1-yl-benzoic acid methyl ester (compound A) (2.1 g) produced by the above reaction was dissolved in anhydrous methylene chloride (20.0 ml). Subsequently, pyridine (900 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (740 μl) were added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added thereto, 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. The residue was purified by column chromatography using a chloroform-acetone system to give 2-(3-chloromethyl-benzoylamino)-5-piperidin-1-yl-benzoic acid methyl ester as a useful intermediate (1.8 g, yield 50%).
Workup
- customAfter the completion of the reaction
- distillationdistilled water
- additionwas added
- extractionthe mixture was subjected to separatory extraction with chloroform
- washThe organic layer was washed with saturated brine
- dry with materialwas dried over sodium sulfate
- concentrationwas then concentrated
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-d2c6025eea3a4c309264514fc5bac7b4
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08134015B2
Reaction notes
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