Hydrochloric Acid → HCID 22935611, compound

HRID 1272350Notes

Reaction equation

Cl.[CH3:2][C:3]1([CH3:34])[CH:7]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[C:6]2[C:14]([CH3:33])=[C:15]([N:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[C:16]([CH3:19])=[C:17]([CH3:18])[C:5]=2[O:4]1.CO.[OH-].[Na+]>C(OCC)(=O)C.C1COCC1>[CH3:2][C:3]1([CH3:34])[CH:7]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[C:6]2[C:14]([CH3:33])=[C:15]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[C:16]([CH3:19])=[C:17]([CH3:18])[C:5]=2[O:4]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 4N hydrogenchloride in ethyl acetate solution (10 ml) was added to a solution of tert butyl 4-(2,2,4,6,7-pentamethyl-3-piperidino-2,3-dihydro-1-benzofuran-5-yl)piperazine carboxylate (1.37 g, 3 mmol) obtained in Example 133 in THF (10 mL)-methanol (10 ml) and the mixture was stirred at 60° C. for 3 hours. After the reaction mixture was cooled to 0° C., the resulting mixture was made weakly alkaline using 1N sodium hydroxide and extracted with ethyl acetate. The organic extract was washed 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 0.89 g (yield 83%) of the title compound as an amorphous powder.

Workup

temperatureAfter the reaction mixture was cooled to 0° C.
extractionextracted with ethyl acetate
extractionThe organic extract
washwas washed saturated aqueous sodium chloride
dry with materialdried over anhydrous sodium sulfate
customthe solvent was removed under reduced pressure
customThe residue was purified with basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-89530c5631f3410c896713f2ff765c01
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208495B2

Reaction notes

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