Dimethylamine → 4-((Dimethylamino)methyl)-4-methyloxazolidin-2-one

HRID 1023478Notes

Reaction equation

HRID 1023478 reaction equation
Cl[CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.C1COCC1.[CH3:15][NH:16][CH3:17]>>[CH3:15][N:16]([CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1)[CH3:17]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-one

Product 1

HCID 593551734-((Dimethylamino)methyl)-4-methyloxazolidin-2-oneYield 32%

Procedure

A solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (2.97 g, 19.9 mmol) in 2.0 M dimethylamine in THF (50 ml, 100 mmol) in a sealed tube was heated to 85° C. for 24 h, cooled to RT, and filtered through a coarse glass filter to remove precipitated dimethylammonium chloride. The filtrate was concentrated, and the residue purified by flash chromatography (3%→10% MeOH in CH2Cl2) to afford the oxazolidinone as a brown oil (1.02 g, 6.45 mmol, 32%), and the dihydrooxazole as a yellow oil (1.62 g, 10.2 mmol, 52%). Rf=0.5 in 10% MeOH in CH2Cl2. 1H NMR (CDCl3, 400 MHz) δ 1.35 (s, 3H), 2.33 (s, 6H), 2.37 (d, J=13.6 Hz, 1H), 2.43 (d, J=14.4 Hz, 1H), 4.02 (d, J=8.4 Hz, 1H), 4.18 (d, J=8.4 Hz, 1H), 5.2 (br s, 1H). ESI/APCI expected for C7H14N2O2: 158.11. Found: 159 (MH+).

Workup

  1. filtrationfiltered through a coarse glass
  2. filtrationfilter
  3. customto remove
  4. customprecipitated dimethylammonium chloride
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified by flash chromatography (3%→10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-af15930ea27b4d8d8668b0ba746c92c4
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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