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

HRID 579527

Reaction equation

HRID 579527 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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)].

Workup

  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)

Sources & evidence

ORD record
ord-6a376953aef548cfa575c005a815ef58
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Linked notes

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