Acetic Acid → HCID 86619193, compound

HRID 1182564Notes

Reaction equation

HRID 1182564 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-164cc8f3ef7b4346a781141165556d37
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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