1,2-Dichloroethane → N-methoxy-N-methyl-3-(pyridin-2-yl)propanamide

HRID 579527

反応式

HRID 579527 の反応式
[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

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 5642923-(Pyridin-2-yl)propanoic acid

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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)].

後処理

  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)

出典と根拠

ORDレコード
ord-6a376953aef548cfa575c005a815ef58
出典データセット
uspto-grants-2015_05
特許番号
US09040703B2

関連ノート

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