2-Chloro-N,N-dimethylethylamine → HCID 58424930, compound

HRID 2409435Notes

Reaction equation

HRID 2409435 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[N:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:8](=[O:15])[N:7]([CH2:16][O:17][CH3:18])[C:6]=2[CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl>CN(C)C=O>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[N:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:8](=[O:15])[N:7]([CH2:16][O:17][CH3:18])[C:6]=2[CH:19]=1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 178496775HCID 178496775, compound

Product 1

HCID 58424930HCID 58424930, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

8-hydroxy-6-(methoxymethyl)benzo[h][1,6]naphthyridine-5(6H)-one (58 mg, 0.22 mmol) and potassium carbonate (94 mg, 0.67 mmol) were dissolved in N,N-dimethylformamide (5 ml) and added with 2-(dimethylamino)ethyl chloride (39 mg, 0.0.27 mmol). The resulting mixture was stirred for 2 hours at 90° C. and poured into ice water. The mixture was extracted with chloroform, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was then purified by flash column chromatography (chloroform:methanol=6:1) to obtain the title compound (53 mg, yield: 73%, white solid).

Workup

  1. extractionThe mixture was extracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe residue was then purified by flash column chromatography (chloroform:methanol=6:1)

Sources & evidence

ORD record
ord-3b62866faf7340e08f42c5eedc2acf70
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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