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

HRID 534190ノート

反応式

HRID 534190 の反応式
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

参加物

6

反応物 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 45358839Piperidin-4-yl-acetic acid ethyl ester hydrochloride

生成物 1

HCID 68385347Ethyl 2-(1-(pyridin-2-yl)piperidin-4-yl)acetate収率 25.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-5afc7cc2a0f8427694dda938d6077503
出典データセット
uspto-grants-2014_10
特許番号
US08853408B2

反応ノート

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