Water → HCID 19029389, compound

HRID 2256300Notes

Reaction equation

HRID 2256300 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:22][CH2:23]Br)[CH2:10][C:11]([N:13]([CH3:21])[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.O.[NH:27]1[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]([CH3:21])[C:11](=[O:12])[CH2:10][CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:22][CH2:23][N:27]2[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2723901PiperonylamineHCID 54542963HCID 54542963, compound

Product 1

HCID 19029389HCID 19029389, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-Dichloro-beta-(2-bromoethyl)-N-methyl-N-(4-chlorophenyl)benzene propanamide (4.6 g) in DMF (60 mL) was treated with 4-piperidone monohydrate hydrochloride (3.94 g) and K2CO3 (5.3 g). The mixture was stirred vigorously at ambient temperature for 120 hours. The reaction mixture was poured into H2O (100 mL) and extracted with EtOAc (2×100 mL). The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give an oil. Silica gel chromatography eluting with 95:5 (CH2Cl2 :MeOH) gave the title compound (2.25 g). Mass spectrum (FAB): 467.1.

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. dry with materialThe organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil
  6. washSilica gel chromatography eluting with 95:5 (CH2Cl2 :MeOH)

Sources & evidence

ORD record
ord-7ae301a7a8aa479fa2e08e232791fbb4
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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