Hydrochloric Acid → N-methyl-4-dimethylamino-2-phenylbutanamide

HRID 231594Notes

Reaction equation

HRID 231594 reaction equation
[CH3:1][NH:2][C:3](=[O:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15]Cl.Cl.CCOCC>C1COCC1.CCCCCC>[CH3:1][NH:2][C:3](=[O:11])[CH:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:15][CH2:14][N:13]([CH3:17])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 79012-Chloro-N,N-dimethylethylamineHCID 81274N-Methyl-2-phenylacetamide

Product 1

HCID 14257912N-methyl-4-dimethylamino-2-phenylbutanamideYield 83.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To 7.46 g (0.05 mol) of N-methyl phenylacetamide (prepared by reaction of phenylacetyl chloride with monomethylamine in CH2Cl2 solvent) dissolved in 70 ml of THF and cooled in an ice-bath to 0°, was added dropwise with stirring under N2, 40 ml (0.10 mol) of a 2.5M solution of N-BuLi in n-hexane. After stirring at 0° for 30 min, the solution was treated by the rapid addition of 5.4 g (0.05 mol) of 2-(dimethylamino)ethyl chloride in 30 ml of THF and then stirred at 0° for 30 min. The reaction mixture was then poured into 250 ml of 1N HCl, ether was added and the aqueous layer was separated, basified with 2.5N NaOH and extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and kugelrohr distilled to afford 9.2 g (83.5%) of N-methyl-4-dimethylamino-2-phenylbutanamide as a viscous. colorless oil; bp 130°-135°/0.1 mm.

Workup

  1. temperaturecooled in an ice-bath to 0°
  2. additionwas added dropwise
  3. stirringAfter stirring at 0° for 30 min
  4. stirringstirred at 0° for 30 min
  5. additionwas added
  6. customthe aqueous layer was separated
  7. extractionextracted with Et2O
  8. extractionThe ether extract
  9. dry with materialwas dried (Na2SO4)
  10. concentrationconcentrated
  11. distillationkugelrohr distilled

Sources & evidence

ORD record
ord-f3af9823b8544fc1843af8567313dc32
Source dataset
uspto-grants-1989_07
Patent number
US04847301

Reaction notes

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