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

HRID 565688Notes

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.[CH2:17]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C([O-])(O)=O.[Na+]>[CH2:17]([CH:24]1[CH2:29][CH2:28][N:27]([CH2:2][C:3]2([CH3:16])[CH2:7][C:6]3[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=3[O:4]2)[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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 (0.85 g), 4-benzylpiperidine (1.1 g), and triethylamine (1.3 mL) was stirred under nitrogen gas at 180° C. for 15 hours. This reaction mixture was diluted with saturated aqueous NaHCO3 and extracted with 2 portions of ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl and dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethanol=10:1) and crystallized from hexane to provide 0.86 g of the title compound. Yield 78%.

Workup

extractionextracted with 2 portions of ethyl acetate
washThe pooled organic layer was washed with water and saturated aqueous NaCl
dry with materialdried over MgSO4
filtrationAfter filtration
concentrationthe filtrate was concentrated under reduced pressure
customcrystallized from hexane

Sources & evidence

ORD record: ord-8980109b47784fe884710fae319b29e9
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172085B2

Reaction notes

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