Acetic Acid → HCID 86619196, compound

HRID 1182605Notes

Reaction equation

HRID 1182605 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]=[C:15]1[O:19][C:17](=[O:18])[CH2:16]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+].[CH3:32][C:33]1[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:34]=1[CH:35]=O.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.CC(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:17](=[O:18])[C:16]([C:15](=[O:19])[CH3:14])=[CH:35][C:34]2[CH:37]=[CH:38][C:39]([CH3:41])=[CH:40][C:33]=2[CH3:32])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

10

Reactant 7

HCID 176Acetic AcidHCID 8082PiperidineHCID 8471TriethylamineHCID 12661DiketeneHCID 618142,4-DimethylbenzaldehydeHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 86619196HCID 86619196, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

506 mg (2.71 mmol) of 1-(t-butoxycarbonyl) piperazine, 273 mg (3.23 mmol) of diketene and 0.562 ml (4.07 mmol) of triethylamine were heated and stirred in 10 ml of toluene at 80° C. for 2 hours. After adding saturated aqueous sodium hydrogencarbonate solution, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. 364 mg (2.71 mmol) of 2,4-dimethylbenzaldehyde was dissolved in 20 ml of 2-propanol. 16.3 mg (0.271 mmol) of piperidine and 22.3 mg (0.271 mmol) of acetic acid were added and stirred at room temperature for 2 days. After the solvent was evaporated under reduced pressure, ethyl acetate was added. The obtained substance was washed with 1 N hydrochloric acid and 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. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customAfter the solvent was evaporated under reduced pressure, ethyl acetate
  5. additionwas added
  6. washThe obtained substance was washed with 1 N hydrochloric acid and saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-6f0840426e844627bd948641729b44d5
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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