Hydrochloric Acid → HCID 9902690, compound

HRID 1272344Notes

Reaction equation

HRID 1272344 reaction equation
Cl.[CH3:2][C:3]1([CH3:33])[CH:7]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[C:6]2[C:13]([CH3:32])=[C:14]([N:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[C:15]([CH3:18])=[C:16]([CH3:17])[C:5]=2[O:4]1.[OH-].[Na+]>C(OCC)(=O)C.C1COCC1>[CH3:2][C:3]1([CH3:33])[CH:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[C:6]2[C:13]([CH3:32])=[C:14]([N:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)[C:15]([CH3:18])=[C:16]([CH3:17])[C:5]=2[O:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10225443HCID 10225443, compound

Product 1

HCID 9902690HCID 9902690, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 4N hydrogenchloride in ethyl acetate (20 ml) was added to a solution of tert butyl 4-(2,2,4,6,7-pentamethyl-3-pyrrolidinyl-2,3-dihydro-1-benzofuran-5-yl)piperazinecarboxylate (3.55 g, 8 mmol) obtained in Example 132 in THF (20 mL) and ethyl acetate (20 ml) and the mixture was stirred at 60° C. for 3 hours. The resulting mixture was cooled to 0° C. made to weakly alkaline using 1N sodium hydroxide aqueous, and extracted with ethyl acetate. The organic extract was washed using saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified with basic silica gel column chromatography (ethyl acetate) to obtain 2.72 g (yield 100%) of the title compound as an amorphous powder.

Workup

  1. temperatureThe resulting mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified with basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-26cc05fe3d6842038e782d4a8fd37965
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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