Hydrochloric Acid → 3,5-Dichloro-4-{4-[3-(trifluoromethyl)phenyl]piperazinyl}phenol

HRID 2242517Notes

Reaction equation

HRID 2242517 reaction equation
C[S-].[Na+].[Cl:4][C:5]1[CH:10]=[C:9]([O:11]C)[CH:8]=[C:7]([Cl:13])[C:6]=1[N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH2:16][CH2:15]1.O.Cl>CN(C=O)C>[Cl:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([Cl:13])[C:6]=1[N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[CH:21]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4378561Sodium methanethiolateHCID 685431491,3-Dichloro-5-methoxy-2-{4-[3-(trifluoromethyl)phenyl]piperazinyl}benzene

Product 1

HCID 685431513,5-Dichloro-4-{4-[3-(trifluoromethyl)phenyl]piperazinyl}phenolYield 63.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

A suspension of 0.8 gram (0.011 mole) of sodium methanethiolate in 25 mL of DMF was stirred, and a solution of 1.8 grams (0.0044 mole) of 1,3-dichloro-5-methoxy-2-{4-[3-(trifluoromethyl)phenyl]piperazinyl}benzene in 40 mL of DMF was added. Upon completion of addition, the reaction mixture was heated to 100° C. where it stirred for two hours. After this time, the reaction mixture was cooled in an ice-water bath and 50 mL of water, followed by 25 mL of an aqueous solution of 10% hydrochloric acid, were added dropwise. The reaction mixture was then saturated with sodium chloride and extracted with two 50 mL portions of diethyl ether. The combined extracts were dried with sodium sulfate, filtered, and concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 1:1 methylene chloride:hexane, then 100% methylene chloride as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.1 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. stirringstirred for two hours
  3. temperatureAfter this time, the reaction mixture was cooled in an ice-water bath
  4. additionwere added dropwise
  5. extractionsaturated with sodium chloride and extracted with two 50 mL portions of diethyl ether
  6. dry with materialThe combined extracts were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure to a residue
  9. customThe residue was purified with column chromatography on silica gel using 1:1 methylene chloride
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf2a33962eb84e36a1a376b072b14f94
Source dataset
uspto-grants-2010_03
Patent number
US07671201B2

Reaction notes

Loading…