Ethyl 4-piperidinecarboxylate → Ethyl 1-(4-methyl-2-pyridyl)piperidine-4-carboxylate

HRID 1775351

反応式

HRID 1775351 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1.CCN(C(C)C)C(C)C>COCCCOCCCO>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1

参加物

5

反応物 3

HCID 70770Ethyl 4-piperidinecarboxylate2 回HCID 81531DiisopropylethylamineHCID 27340872-Bromo-4-methylpyridine

生成物 1

HCID 62007359Ethyl 1-(4-methyl-2-pyridyl)piperidine-4-carboxylate収率 56%

試薬・触媒・溶媒 1

HCID 669843-(3-Methoxypropoxy)-1-propanol溶媒

反応条件

温度
150 °C

実験手順

2-Bromo-4-methylpyridine (860 mg, 5 mmol), ethyl piperidine-4-carboxylate (865 mg, 5.5 mmol) and DIPEA (958 μl, 5.5 mmol) were mixed in dipropyleneglycolmonomethylether (10 ml) and stirred at 150° C. overnight. Additional ethyl piperidine-4-carboxylate (865 mg, 5.5 mmol) was added and stirring was continued at 150° C. for 24 hours. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography (silica, gradient from 0 to 30% ethyl acetate in DCM) to give 700 mg of a brown solid (2.8 mmol, 56%) MS (multi-mode) m/z=249.1 [M+1]+.

後処理

  1. stirringstirring
  2. waitwas continued at 150° C. for 24 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography (silica, gradient from 0 to 30% ethyl acetate in DCM)

出典と根拠

ORDレコード
ord-4094ab713b40481c8bd9863b0bf14f04
出典データセット
uspto-grants-2016_02
特許番号
US09260441B2

関連ノート

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