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

HRID 579527

반응식

HRID 579527 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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)].

후처리

  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)

출처 및 근거

ORD 기록
ord-6a376953aef548cfa575c005a815ef58
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

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