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

HRID 2063796Notes

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-1d9070a206244d858be776a0ffbfba6e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288390B2

Reaction notes

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