Benzylamine → Benzyl-(6-fluoroindan-1-ylidene)-amine

HRID 2175050Notes

Reaction equation

HRID 2175050 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=O)=[CH:4][CH:3]=1.[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:12]([N:19]=[C:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=2)[CH2:6][CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 15194646-Fluoro-1-indanone

Product 1

HCID 90019076Benzyl-(6-fluoroindan-1-ylidene)-amineYield 100%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

Combine 6-fluoroindan-1-one (14.57 g, 97.04 mmol) and benzylamine (10.60 mL, 97.04 mmol) in toluene (75 mL). Add p-toluenesulfonic acid monohydrate (0.923 g, 4.85 mmol). Attach a reflux condenser and heat the mixture under nitrogen to reflux over six hours, then stir at room temperature for 14 hours. Extract the mixture with ethyl acetate and water. Dry the resulting organics with magnesium sulfate, filter, and concentrate in vacuo to give the title compound as a red oil (23.22 g, 100%). MS (ES) m/z=240 [M+1].

Workup

  1. temperatureheat the mixture under nitrogen
  2. temperatureto reflux over six hours
  3. extractionExtract the mixture with ethyl acetate and water
  4. dry with materialDry the resulting organics with magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b92abb67c7414d4ebb2fedfe88909b9d
Source dataset
uspto-grants-2015_06
Patent number
US09062050B2

Reaction notes

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