Potassium Carbonate → HCID 19911450, compound

HRID 1533903Notes

Reaction equation

HRID 1533903 reaction equation
[ClH:1].[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7]Cl.[F:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=1[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[ClH:2].[ClH:1].[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)=[CH:12][C:11]=1[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679814-Fluoro-m-toluidineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 19911450HCID 19911450, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 56.3 g (0.315 mol) of bis(2-chloroethyl)amine hydrochloride and 35.9 g (0.287 mol) of 4-fluoro-3-methylbenzeneamine in 500 mL of absolute ethanol was heated at reflux for 24 h under a nitrogen atmosphere. The mixture was cooled and 65.3 g (0.473 mol) of anhydrous potassium carbonate was added and heating was continued for 24 h. The hot mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was triturated with ethyl acetate to yield a crude solid. This solid was converted to the base and purified by column chromatography using 500 g of silica gel on a 30 cm×10 cm column, eluted with methanol. The fractions containing the product were combined and concentrated. The residue was partitioned between water and ethyl ether. The ethyl ether layer was washed with water, dried (MgSO4) and concentrated under reduced pressure to yield 9.3 g (14%) of a light-pink oil. A portion of the oil was converted to the dihydrochloric acid salt and the solid was recrystallized from 2-propanol to yield a white solid, mp 188°-191° C.

Workup

  1. temperatureat reflux for 24 h under a nitrogen atmosphere
  2. temperatureThe mixture was cooled
  3. temperatureheating
  4. filtrationThe hot mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was triturated with ethyl acetate
  7. customto yield a crude solid
  8. custompurified by column chromatography
  9. washeluted with methanol
  10. additionThe fractions containing the product
  11. concentrationconcentrated
  12. customThe residue was partitioned between water and ethyl ether
  13. washThe ethyl ether layer was washed with water
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7431e93c61004d089becfd2d5d65f3bb
Source dataset
uspto-grants-1992_02
Patent number
US05086055

Reaction notes

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