2,2,2-Trifluoroacetophenone → HCID 11323391, compound

HRID 605416Notes

Reaction equation

HRID 605416 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH3:13][C@@H:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:15]1([C@H:14]([N:21]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([F:12])([F:11])[F:1])[CH3:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 99052,2,2-TrifluoroacetophenoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 11323391HCID 11323391, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2,2,2-trifluoroacetophenone (7.0 g, 40 mmol), R-(+)-α-methylbenzylamine (7.75 mL, 60 mmol), and p-toluenesulfonic acid monohydrate (0.77g, 4.0 mmol) in toluene (40 mL) was refluxed for 18 hours with a Dean-Stark trap. After cooling, the reaction mixture was diluted with toluene (50 mL), washed with 5% NaOH (1×50 mL), saturated NH4Cl (4×30 mL) and brine, dried over MgSO4, concentrated and dried at room temperature in vacuum to give the title compound as pale yellow liquid (11.1 g).

Workup

  1. temperatureAfter cooling
  2. washwashed with 5% NaOH (1×50 mL), saturated NH4Cl (4×30 mL) and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customdried at room temperature in vacuum

Sources & evidence

ORD record
ord-1a848b902fb641e491cf2ae430be8f6a
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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