Toluene → HCID 59006376, compound

HRID 2378946Notes

Reaction equation

HRID 2378946 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.C(OCC)(=O)C.[F:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21].[CH3:26][O:27][CH:28]([O:44][CH3:45])[CH2:29][NH:30][CH:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:45][O:44][CH:28]([O:27][CH3:26])[CH2:29][N:30]([CH:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[CH2:33][CH2:32]1)[C:1]([NH:21][C:20]1[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=1[F:18])=[O:2]

Participants

8

Reactant 6

HCID 1140TolueneHCID 6371PhosgeneHCID 8857Ethyl AcetateHCID 95842-FluoroanilineHCID 516892Sodium BicarbonateHCID 59006342HCID 59006342, compound

Product 1

HCID 59006376HCID 59006376, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20% Phosgene in toluene (4.0 ml, 7.6 mmol) was diluted with ethyl acetate (20 ml, 205 mmol). 2-Fluoroaniline (0.600 ml, 6.2 mmol) was added to the mixture in one portion causing a white precipitate. Mixture was heated to reflux and held with stirring for 1 hour. Mixture was concentrated by roto-vap. Residue was dissolved in a small amount of dichloromethane. Resulting solution was added to a mixture of tert-butyl 4-(2,2-dimethoxyethylamino)piperidine-1-carboxylate (1.99 g, 6.9 mmol), dichloromethane (30 mL) and aqueous sodium bicarbonate (15 mL) while stirring vigorously. Reaction stirred at room temperature for 2 hours. Layers were separated and the aqueous phase was discarded. Material was washed twice with 1N hydrochloric acid and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as yellow oil in 53% yield. MS (M−H)−=424.1.

Workup

  1. temperatureMixture was heated
  2. temperatureto reflux
  3. concentrationMixture was concentrated by roto-vap
  4. dissolutionResidue was dissolved in a small amount of dichloromethane
  5. stirringwhile stirring vigorously
  6. customReaction
  7. stirringstirred at room temperature for 2 hours
  8. customLayers were separated
  9. washMaterial was washed twice with 1N hydrochloric acid
  10. filtrationfiltered
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5aa9c8c10c4d4873993d58b8df040419
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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