Sodium Hydroxide → HCID 22458126, compound

HRID 2184829Notes

Reaction equation

HRID 2184829 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-e5ff2f347bc64e46a9f33680fc4e4e9d
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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