Toluene → HCID 13713311, compound

HRID 1780935Notes

Reaction equation

HRID 1780935 reaction equation
[N+](C1C=CC(CCC(C)=O)=CC=1)([O-])=O.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl.[C:34]1([CH:40]([OH:56])[CH2:41][NH:42][CH:43]([CH3:55])[CH2:44][CH2:45][C:46]2[CH:51]=[CH:50][C:49]([N+:52]([O-:54])=[O:53])=[CH:48][CH:47]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O>[C:34]1([CH:40]([OH:56])[CH2:41][NH:42][CH:43]([CH3:55])[CH2:44][CH2:45][C:46]2[CH:47]=[CH:48][C:49]([N+:52]([O-:54])=[O:53])=[CH:50][CH:51]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 122356724-(4-Nitrophenyl)butan-2-oneHCID 13713312HCID 13713312, compound

Product 1

HCID 13713311HCID 13713311, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.0 g. (25.9 mM) of 2-amino-1-phenyletkanol and 3.55 g. (25.9 mM) of methyl 2-(4-nitrophenyl)ethyl ketone in 60 ml. of toluene containing 10 mg. of para-toluenesulfonic acid was heated at reflux for six hours in a flask equipped with a Dean-Stark trap. The water that formed during the reaction was removed via the trap, and then the reaction mixture was cooled to room temperature and concentrated to dryness by evaporation of the solvent under reduced pressure. The solid product that remained was dissolved in 50 ml. of tetrahydrofuran and the solution was heated to reflux. A solution of 13.5 ml. of 2N borane-methyl sulfide complex in tetrahydrofuran was then added dropwise to the reaction mixture, and the mixture was refluxed for an additional ninety minutes. After cooling the reaction mixture to room temperature, it was diluted by addition of diethyl ether saturated with hydrogen chloride. The precipitate that formed was collected by filtration and crystallized from ethanol and diethyl ether to give 3.29 g. of 1-phenyl-2-[1-methyl-3-(4-nitrophenyl)-propylamino]ethanol hydrochloride. M.P. 203°-213° C.

Workup

  1. temperatureat reflux for six hours in a flask
  2. customequipped with a Dean-Stark trap
  3. customwas removed via the trap
  4. concentrationconcentrated to dryness by evaporation of the solvent under reduced pressure
  5. dissolutionThe solid product that remained was dissolved in 50 ml
  6. temperatureof tetrahydrofuran and the solution was heated to reflux
  7. additionof 2N borane-methyl sulfide complex in tetrahydrofuran was then added dropwise to the reaction mixture
  8. temperaturethe mixture was refluxed for an additional ninety minutes
  9. temperatureAfter cooling the reaction mixture to room temperature
  10. additionit was diluted by addition of diethyl ether saturated with hydrogen chloride
  11. customThe precipitate that formed
  12. filtrationwas collected by filtration
  13. customcrystallized from ethanol and diethyl ether
  14. customto give 3.29 g

Sources & evidence

ORD record
ord-6069f006ac0d49bf835b01ab585ad211
Source dataset
uspto-grants-1997_05
Patent number
US05631298

Reaction notes

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