Benzoyl chloride, 3-chloro- → HCID 53307822, compound

HRID 1846643Notes

Reaction equation

HRID 1846643 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

HCID 69252Benzoyl chloride, 3-chloro-HCID 67322151HCID 67322151, compound

Product 1

HCID 53307822HCID 53307822, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

Workup

  1. customvolatiles are removed under reduced pressure
  2. dissolutionThe residue is dissolved in dichloromethane
  3. washthe mixture is washed with 5% aqueous NaOH solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe mixture is concentrated under reduced pressure
  6. customthe crude mass purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-8fd6f550abaa4c46934a41fe2361e2f4
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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