Piperidine → 5-Fluoro-3-(2-(piperidin-1-yl)ethyl)-1H-indole

HRID 1095513Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[NH:12][CH:11]=1>O1CCOCC1>[F:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:9][CH2:8][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

Piperidine (3.52 g, 4.08 ml, 41.3 mmol) was dissolved in abs dioxane (100 ml), 3-(2-bromo-ethyl)-5-fluoro-1H-indole (5.00 g, 20.7 mmol) was added at RT and the mixture was stirred at 70° C. for 16 h. The solution was concentrated, the residue was taken up in CHCl3 (150 ml) and the mixture was washed with water (2×50 ml). The organic phase was dried over Na2SO4, filtered and concentrated i. vac. The residue obtained was purified by flash chromatography with 200 g of silica gel and ethyl acetate/ethanol (9:1→1:2).

Workup

concentrationThe solution was concentrated
washthe mixture was washed with water (2×50 ml)
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated i
customThe residue obtained
customwas purified by flash chromatography with 200 g of silica gel and ethyl acetate/ethanol (9:1→1:2)

Sources & evidence

ORD record: ord-29e50087df7a498cbdf9b5bf2c0cb114
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138187B2

Reaction notes

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