Hydrochloric Acid → HCID 18955938, compound

HRID 2379685Notes

Reaction equation

HRID 2379685 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]([Cl:15])[C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=2)=[CH:4][CH:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:37].Cl.Cl>C(OCC)(=O)C>[ClH:15].[ClH:37].[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]([N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)[C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 531671-MethylpiperazineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 189559361-[(4-Bromophenyl)chloromethyl]-3-methoxybenzene

Product 1

HCID 18955938HCID 18955938, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The crude benzhydryl chloride from above (6.5 g, 21 mmole) was added to 8.3 g (83 mmole) of 1-methylpiperazine and the reaction was heated to reflux for four hours. After cooling to room temperature, the mixture was dissolved in 100 ml of ethyl acetate and washed with two 150 ml portions of 1.0M sodium hydroxide, followed by two 150 ml portions of water and 100 ml of saturated aqueous sodium chloride. The solution was dried over magnesium sulfate and the solvent removed to give 6.5 g of crude product as an oil. The product was purified by chromatography on silica gel (Waters Prep 500) with dichloromethane:ethanol:triethylamine (100:0.2:0.1) to give a colorless oil. A portion was converted to the dihydrochloride salt with ethanolic hydrochloric acid and precipitated from ethanol with 1:1 hexane:diethyl ether to give 1-(α-(4-bromophenyl)-3-methoxybenzyl)-4-methylpiperazine dihydrochloride as a white powdery solid, mp. 195°-197° C. Calc. for C19H23BrN2O2HCl: C, 50.91; H, 5.62; N, 6.25; Total halogen calc. as Cl, 23.73. Found: C, 51.00; H, 5.66; N, 6.23; Total halogen calc. as Cl, 23.78.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for four hours
  3. washwashed with two 150 ml portions of 1.0M sodium hydroxide
  4. dry with materialThe solution was dried over magnesium sulfate
  5. customthe solvent removed
  6. customto give 6.5 g of crude product as an oil
  7. customThe product was purified by chromatography on silica gel (Waters Prep 500) with dichloromethane:ethanol:triethylamine (100:0.2:0.1)
  8. customto give a colorless oil
  9. customprecipitated from ethanol with 1:1 hexane

Sources & evidence

ORD record
ord-17221f652e88417aafa8bf505a8a3050
Source dataset
uspto-grants-1994_11
Patent number
US05364843

Reaction notes

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