Benzoyl chloride, 3-chloro- → HCID 53307822, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:16][CH2:15]1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](Cl)=[O:33]>C(#N)C>[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32]([NH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:18][CH2:19]1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6])=[O:33]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of compound 0.20 g (0.53 mmol) of 3-amino-N-cyclopropyl-4-[4-(2-piperidin-1-yl-ethyl)-piperidin-1-yl]-benzamide in acetonitrile (5 mL) is added 0.04 mL (0.31 mmol) 3-chlorobenzoyl chloride. The mixture is stirred at room temperature for 30 minutes then volatiles are removed under reduced pressure. The residue is dissolved in dichloromethane and the mixture is washed with 5% aqueous NaOH solution followed by water and then dried over anhydrous magnesium sulfate. The mixture is concentrated under reduced pressure and the crude mass purified by flash silica gel chromatography to yield 0.040 g (15%) of 3-(3-Chloro-benzoylamino)-N-cyclopropyl-4-[4-(2-piperidin-1-yl-ethyl)-piperidin-1-yl]-benzamide (112). [M+H]+=479.4