Triethylamine → 2,3-Dihydro-2,4,6,7-tetramethyl-2-[[4-(2-phenylethyl)-1-piperidinyl]methyl]-5-benzofuranamine

HRID 565686Notes

Reaction equation

Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[C:17]1([CH2:23][CH2:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C([O-])(O)=O.[Na+]>[CH3:16][C:3]1([CH2:2][N:28]2[CH2:29][CH2:30][CH:25]([CH2:24][CH2:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:26][CH2:27]2)[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1

Participants

Conditions

Temperature: 180 °C

Procedure

In an autoclave, a mixture of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.5 g), 4-(2-phenylethyl)piperidine (2.0 g), and triethylamine (5.3 g) was stirred under argon gas at 180° C. for 15 hours. After cooling, the reaction mixture was diluted with saturated aqueous NaHCO3 and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1) and recrystallized from diisopropyl ether to provide 0.88 g of the title compound. Yield 42%.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washThe extract was washed with saturated aqueous NaCl
dry with materialdried over MgSO4
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1)
customrecrystallized from diisopropyl ether

Sources & evidence

ORD record: ord-48191aeed5bb4d0e9fa03d8a3961a655
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172085B2

Reaction notes

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