Sodium Hydroxide → HCID 22458126, compound

HRID 1420570Notes

Reaction equation

HRID 1420570 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[CH2:18][CH2:17]1.[OH-].[Na+]>C(O)CCC.O>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 737542-(Trifluoromethoxy)anilineHCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 22458126HCID 22458126, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A solution of 2.09 g of 2-trifluoromethoxyaniline and 3.15 g of 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine in 20 mL of n-butanol was stirred at 100° C. for 2 hrs. The mixture was then cooled, diluted with H2O, alkalinized with 2 N NaOH and extracted with CHCl3. The organic phase was dried on anhydrous Na2SO4, evaporated until dry and the crude purified via flash chromatography (EtOAc-petrolium ether 3:7) and subsequently crystallized from EtOH giving 0.55 g (12%) of the title compound. Melting point: 69.5-71° C.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with CHCl3
  3. dry with materialThe organic phase was dried on anhydrous Na2SO4
  4. customevaporated
  5. customuntil dry
  6. customthe crude purified via flash chromatography (EtOAc-petrolium ether 3:7)
  7. customsubsequently crystallized from EtOH giving 0.55 g (12%) of the title compound

Sources & evidence

ORD record
ord-b16d0a437d924e3f91fd3145c2cc6e8a
Source dataset
uspto-grants-2000_06
Patent number
US06071920

Reaction notes

Loading…