1,2-二氯乙烷 → N-methoxy-N-methyl-3-(pyridin-2-yl)propanamide

HRID 579527

反应方程式

HRID 579527 反应方程式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]([OH:11])=O.Cl.[CH3:13][NH:14][O:15][CH3:16].C(Cl)CCl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.O>[CH3:16][O:15][N:14]([CH3:13])[C:9](=[O:11])[CH2:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

参与物

8

反应物 4

HCID 111,2-二氯乙烷HCID 8471三乙胺HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 5642923-吡啶-2-基-丙酸

产物 1

HCID 78981096N-methoxy-N-methyl-3-(pyridin-2-yl)propanamide收率 79.3%

试剂、催化剂与溶剂 3

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6344二氯甲烷溶剂

实验过程

A solution of 3-pyridin-2-yl-propionic acid (1.0 g, 6.62 mmol), DMAP (10 mg), and N,O-dimethylhydroxylamine hydrochloride (679 g, 7.0 mmol) and EDC (1.34 g, 7.0 mmol) in dichloromethane (40 mL) was treated with triethylamine (2.8 mL, 20.0 mmol). After stirring at room temperature overnight, the solution was poured into water, extracted with ethyl acetate (3×) and the combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by column chromatography (silica gel, 30-100% ethyl acetate in heptane) gave N-methoxy-N-methyl-3-(pyridin-2-yl)propanamide (1.02 g, 78%) as a colorless oil. ESI MS found for C10H14N2O2 m/z [195.1 (M+1)].

后处理

  1. extractionextracted with ethyl acetate (3×)
  2. washthe combined organic phase was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (silica gel, 30-100% ethyl acetate in heptane)

来源与证据

ORD记录
ord-6a376953aef548cfa575c005a815ef58
来源数据集
uspto-grants-2015_05
专利号
US09040703B2

关联笔记

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