Tetrahydrofuran → HCID 22111017, compound

HRID 565680Notes

Reaction equation

[CH3:1][C:2]1([CH2:15][N:16]2[CH2:21][CH:20]=[C:19]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:23]=3)[CH2:18][CH2:17]2)[CH2:6][C:5]2[C:7]([CH3:14])=[C:8]([NH2:13])[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1.O1CCCC1>[Pt]=O.CO>[CH3:1][C:2]1([CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:23]=3)[CH2:20][CH2:21]2)[CH2:6][C:5]2[C:7]([CH3:14])=[C:8]([NH2:13])[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2,3-Dihydro-2,4,6,7-tetramethyl-2-[[1,2,3,6-tetrahydro-4-(1-phenyl-3-indolyl)-1-pyridyl]methyl]-5-benzofuranamine (0.36 g), platinum oxide (72 mg), tetrahydrofuran (2 mL) and methanol (4 mL) was stirred for 3.5 hours at 60° C. under hydrogen atmosphere. The mixture was cooled, the catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=5:1) to afford 2,3-Dihydro-2,4,6,7-tetramethyl-2-[[4-(1-phenyl-3-indolyl)-1-piperidinyl]methyl]-5-benzofuranamine. This was dissolved in methanol and to the resulting solution 1 equivalent of oxalic acid solution in methanol was added. The mixture was concentrated and to the residue was added ethanol and diethyl ether. The resulting powdery product was collected to afford the 0.10 g of the title compound. Yield 24%.

Workup

temperatureThe mixture was cooled
customthe catalyst was removed by filtration
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-740995aa09004e9b805c4e3e48ca3852
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172085B2

Reaction notes

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