2-Bromopyridine → Ethyl 2-(1-(pyridin-2-yl)piperidin-4-yl)acetate

HRID 534190Notes

Reaction equation

Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1>CN(C=O)C.O>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a stirred solution of ethyl 2-(piperidin-4-yl)acetate, hydrochloride (2.0 g, 9.63 mmol) in DMF (40 mL) was added K2CO3 (3.99 g, 28.9 mmol) followed by 2-bromopyridine (1.521 g, 9.63 mmol) and stirred at 130° C. for 16 h. Reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with water (2×100 mL), brine (100 mL) and dried over Na2SO4 filtered and concentrated under reduced pressure. The residues was purified by column chromatography using 100-200 silica gel by eluting with 20% ethyl acetate in petroleum ether to afford ethyl 2-(1-(pyridin-2-yl)piperidin-4-yl)acetate (600 mg, 19.86% yield) as color less liquid. LCMS (ES) m/e 249.20 (M+H)+.

Workup

customReaction mixture
extractionextracted with ethyl acetate (2×100 mL)
washThe combined organic layer was washed with water (2×100 mL), brine (100 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residues was purified by column chromatography
washby eluting with 20% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-5afc7cc2a0f8427694dda938d6077503
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853408B2

Reaction notes

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