Tetrahydrofuran → HCID 54056363, compound

HRID 2290457Notes

Reaction equation

HRID 2290457 reaction equation
Cl.Cl.[C:3]([OH:11])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:12][C:13]1[CH:22]=[CH:21][C:16]([CH:17]=[CH:18][CH2:19]Cl)=[CH:15][CH:14]=1.[CH2:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH3:24].C1(N)C(F)=C(F)C(F)=C([NH2:39])C=1F.Cl.Cl.O1[CH2:48][CH2:47]CC1>>[Cl:12][C:13]1[CH:22]=[CH:21][C:16]([CH:17]=[CH:18][CH2:19][N:39]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][C:7]3[CH:8]=[CH:9][C:4]([C:3]([O:11][CH2:47][CH3:48])=[O:10])=[CH:5][CH:6]=3)[CH2:23][CH2:24]2)=[CH:15][CH:14]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 53728250p-Chlorocinnamyl chlorideHCID 67526975HCID 67526975, compound

Product 1

HCID 54056363HCID 54056363, compound

Procedure

A mixture of 33.5 g. (0.1 mole) ethyl 4-[2-piperazin-1-yl)-ethyl]-benzoate dihydrochloride, 19.6 g. (105 mmole) 4-chlorocinnamyl chloride, 40.8 g. (0.4 mole) anhydrous triethylamine and 400 ml. anhydrous tetrahydrofuran is maintained at reflux temperature for 24 hours and subsequently evaporated in a vacuum. The residue is mixed with methylene chloride and water. After vigorous mixing up, the phases are separated. The methylene chloride phase is washed several times with water, then dried with anhydrous sodium sulphate and evaporated. The residue is dissolved in a little methylene chloride and hydrogen chloride-containing diethyl ether, whereupon the dihydrochloride precipitates out. This is filtered off with suction, washed with diethyl ether, digested with hot ethanol and finally dried to give 39.5 g. of the dihydrochloride of the desired compound; m.p. 283°-285° C.

Workup

  1. additionA mixture of 33.5 g
  2. temperatureat reflux temperature for 24 hours
  3. customsubsequently evaporated in a vacuum
  4. additionThe residue is mixed with methylene chloride and water
  5. additionAfter vigorous mixing up
  6. customthe phases are separated
  7. washThe methylene chloride phase is washed several times with water
  8. dry with materialdried with anhydrous sodium sulphate
  9. customevaporated
  10. dissolutionThe residue is dissolved in a little methylene chloride and hydrogen chloride-
  11. additioncontaining diethyl ether
  12. customwhereupon the dihydrochloride precipitates out
  13. filtrationThis is filtered off with suction
  14. washwashed with diethyl ether
  15. customfinally dried
  16. customto give 39.5 g

Sources & evidence

ORD record
ord-da32054f7bab49b0b88fe8353c7ae2c9
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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