Benzoyl chloride, 3-chloro- → HCID 68304434, compound

HRID 1846668Notes

Reaction equation

HRID 1846668 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[NH2:19])[CH2:8][CH2:7]1)[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26]>C(#N)C>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[NH:19][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][CH:30]=[C:22]([Cl:21])[CH:23]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 67323853HCID 67323853, compound

Product 1

HCID 68304434HCID 68304434, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.710 g (2.39 mmol) of [1-(2-amino-4-chloro-phenyl)-piperidin-4-yl]-acetic acid ethyl ester in acetonitrile (25 mL) is added 0.37 mL (2.9 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred at room temperature for 2 hours then concentrated under reduced pressure. The residue is treated with a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The combined organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide 0.590 g (56.7%) of {1-[4-chloro-2-(3-chloro-benzoylamino)-phenyl]-piperidin-4-yl}-acetic acid ethyl ester as a white solid.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. additionThe residue is treated with a saturated aqueous solution of ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-a5312fabbe474119be3d663738ff823c
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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