Phenethylamine → 3-(benzyl-methyl-amino)-N-methoxy-N-methyl-propionamide

HRID 2218081Notes

Reaction equation

HRID 2218081 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](CN)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:17][CH2:18][C:19]([N:21]([O:23][CH3:24])[CH3:22])=[O:20].[C:25](#[N:27])C>>[CH2:7]([N:27]([CH3:25])[CH2:17][CH2:18][C:19]([N:21]([O:23][CH3:24])[CH3:22])=[O:20])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 1001PhenethylamineHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 112063733-bromo-N-methoxy-N-methylpropanamide

Product 1

HCID 597695563-(benzyl-methyl-amino)-N-methoxy-N-methyl-propionamideYield 82%

Procedure

Add potassium carbonate (63.50 g, 459 mmol) to a stirred solution of N-benzylmethylamine (14.8 mL, 115 mmol), 3-bromo-N-methoxy-N-methyl-propionamide (22.47 g, 115 mmol, prepared according to Jacobi, P. A.; Blum, C. A.; DeSimone, R. W.; Udodong, U. E. S. J. Am. Chem. Soc. 1991, 113, 5384-5392), and anhydrous acetonitrile (460 mL). Heat the reaction to reflux under nitrogen for 3 hours. Cool the reaction to room temperature and filter the reaction through Celite®. Wash the Celite® with ethyl acetate and concentrate on a rotary evaporator to give the crude product. Purify the crude product by flash chromatography on silica gel eluting with 0.5% concentrated ammonium hydroxide/5% ethanol/chloroform to yield 22.31 g (82%) of 3-(benzyl-methyl-amino)-N-methoxy-N-methyl-propionamide: mass spectrum (ion spray) m/z=237.1(M+1); 1H NMR (CDCl3) δ 7.31-7.21 (m, 5H), 3.65 (s, 3H), 3.53 (s, 2H), 3.17 (s, 3H), 2.80-2.76 (m, 2H), 2.67-2.63 (m, 2H), 2.23 (s, 3H).

Workup

  1. customprepared
  2. temperatureHeat
  3. customthe reaction
  4. temperatureto reflux under nitrogen for 3 hours
  5. temperatureCool
  6. customthe reaction to room temperature
  7. filtrationfilter
  8. customthe reaction through Celite®
  9. washWash the Celite® with ethyl acetate
  10. concentrationconcentrate on a rotary evaporator
  11. customto give the crude product
  12. customPurify the crude product by flash chromatography on silica gel eluting with 0.5% concentrated ammonium hydroxide/5% ethanol/chloroform

Sources & evidence

ORD record
ord-410dc343372d4812b757f984641d175f
Source dataset
uspto-grants-2008_08
Patent number
US07410982B2

Reaction notes

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