Water → 1-(4-Fluoro-2-methoxyphenyl)piperazine

HRID 1384841Notes

Reaction equation

HRID 1384841 reaction equation
O.Cl.[F:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([O:11][CH3:12])[CH:5]=1.Cl.Cl[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Cl>ClC1C=CC=CC=1>[F:3][C:4]1[CH:10]=[CH:9][C:7]([N:8]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[C:6]([O:11][CH3:12])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 211838464-Fluoro-2-methoxyaniline--hydrogen chloride (1/1)

Product 1

HCID 104886541-(4-Fluoro-2-methoxyphenyl)piperazineYield 25%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
20 °C

Procedure

9 ml of chlorobenzene and H2O were distilled from a solution of 1.14 g of p-TosOH (6.03×10−3 moles) in 200 ml of chlorobenzene. The solution was cooled to 20° C. and then 1.19 g of 4-fluor-2-methoxyaniline hydrochloride (6.7×10−3 moles) and 1.31 g of bis (2-chloroethyl)amine hydrochloride (7.36×10−3 moles) were added. The reaction was held under reflux for 72 hours after which the solvent was removed and the residue was extracted with 5 ml of NaOH 2N and 30 ml of toluene. The organic phase was washed with H2O, was dried with Na2SO4 and the toluene was removed. The product was purified by silica column using dichloromethane/MeOH (9:1) as mobile phase. An oil was obtained. Yield: 25%.

Workup

  1. temperatureunder reflux for 72 hours after which the solvent
  2. customwas removed
  3. extractionthe residue was extracted with 5 ml of NaOH 2N and 30 ml of toluene
  4. washThe organic phase was washed with H2O
  5. dry with materialwas dried with Na2SO4
  6. customthe toluene was removed
  7. customThe product was purified by silica column
  8. customAn oil was obtained

Sources & evidence

ORD record
ord-c557cffd5cd54ab384ce3a75a9b6c4f2
Source dataset
uspto-grants-2001_07
Patent number
US06262056B1

Reaction notes

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