Hydrochloric Acid → Propiophenone, 3-(benzylmethylamino)-, hydrochloride

HRID 1199719Notes

Reaction equation

HRID 1199719 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[ClH:10].[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])[CH3:12].[CH2:20]=O>C(O)C>[ClH:10].[CH3:1][N:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:20][CH2:12][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 712Formaldehyde2×HCID 7410AcetophenoneHCID 7669N-Methylbenzylamine

Product 1

HCID 3034159Propiophenone, 3-(benzylmethylamino)-, hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
24 °C

Procedure

To a five liter, 3-necked, round bottom flask equipped with two condensers were added 558.0 g (4.6 mol) methylbenzylamine and 500 ml of ethanol. The solution was stirred while an ethanolic solution of hydrochloric acid (170.0 g of acid dissolved in 2500 ml of ethanol) was added over a one hour period. After hydrochloric acid addition was complete, acetophenone (552.5 g; 4.6 mol) and paraformaldehyde (207.0 g; 6.9 mol) were added. The solution was heated until the liquid began to reflux and then stirred at that temperature overnight. The next morning an additional 137.0 g (4.6 mol) of paraformaldehyde were added and the reaction solution was stirred for an additional five hours at the reflux temperature. The solution was then cooled to room temperature (24° C.) and the solids which precipitated were collected by filtration, washed with ethanol and dried in a vacuum oven at 40° C. to provide 1090.0 g (82.0% yield) of 3-[methyl(phenylmethyl)amino]-1-phenyl-1-propanone hydrochloride.

Workup

  1. customTo a five liter, 3-necked, round bottom flask equipped with two condensers
  2. additionwas added over a one hour period
  3. temperatureThe solution was heated until the liquid
  4. temperatureto reflux
  5. stirringthe reaction solution was stirred for an additional five hours at the reflux temperature
  6. customthe solids which precipitated
  7. filtrationwere collected by filtration
  8. washwashed with ethanol
  9. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-79048e4dd4a045a3a3ff541bc7f9f7fe
Source dataset
uspto-grants-1990_02
Patent number
US04902710

Reaction notes

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