Hydrochloric Acid → 1-(2,4,6,7-Tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

HRID 1850387Notes

Reaction equation

[CH3:1][CH:2]1[CH2:6][C:5]2[C:7]([CH3:26])=[C:8]([N:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1.Cl.[OH-].[Na+]>C(OCC)(=O)C>[CH3:1][CH:2]1[CH2:6][C:5]2[C:7]([CH3:26])=[C:8]([N:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

tert-butyl 4-(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine-1-carboxylate (16.1 g, 44.7 mmol) synthesized in Reference Example 55 was added to an ethyl acetate solution containing 2N hydrogen chloride, and the mixture was stirred at 50° C. for 3 hours. The reaction solution was poured into an aqueous solution of 2N sodium hydroxide, and the mixture was extracted using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous sodium sulfate. After that, the solvent was removed under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (ethyl acetate-methanol 90:10) to give 11.3 g of the title compound as an oily product (yield: 97%).

Workup

extractionthe mixture was extracted
washThe extract was washed with saturated saline
customdried
customAfter that, the solvent was removed under reduced pressure
customthe obtained residue was purified by basic silica gel column chromatography (ethyl acetate-methanol 90:10)

Sources & evidence

ORD record: ord-4b7878c8f06c4d35b65dbca13d66a9f8
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957069B2

Reaction notes

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