Acetic Acid → HCID 86619193, compound

HRID 1727885Notes

Reaction equation

HRID 1727885 reaction equation
[O:1]=[C:2]([CH3:15])[CH2:3][CH2:4][N-:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[CH:20]=O.N1CCCCC1.C(O)(=[O:34])C>CC(O)C>[C:2]([C:3](=[CH:20][C:19]1[CH:18]=[C:17]([Cl:16])[CH:24]=[C:23]([Cl:25])[CH:22]=1)[C:4]([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:34])(=[O:1])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 357463,5-DichlorobenzaldehydeHCID 86619194HCID 86619194, compound

Product 1

HCID 86619193HCID 86619193, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.22 g (10.1 mmol) of 3-oxo-N-(3-phenylpropyl)butylamide and 1.77 g (10.1 mmol) of 3,5-dichlorobenzaldehyde were dissolved in 30 ml of 2-propanol. 86.0 mg (1.01 mmol) of piperidine and 60.7 mg (1.01 mmol) of acetic acid were added and stirred at room temperature for one day. After the solvent was evaporated under reduced pressure, ethyl acetate was added thereto. The reaction mixture was washed with 1 N hydrochloric acid and then with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1) to obtain the title compound.

Workup

  1. customAfter the solvent was evaporated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washThe reaction mixture was washed with 1 N hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-8059b7c1ad8247368b409d6c31c1971a
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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