Potassium Hydroxide → 1-(2-Fluoro-6-methoxyphenyl)piperazine

HRID 1533859

Reaction equation

HRID 1533859 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:3]=1[NH2:4].Br.Br[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]Br.[OH-].[K+].[OH-].[Na+]>O>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:3]=1[N:4]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 4592532-Fluoro-6-methoxyanilineHCID 12692731Ethanamine, 2-bromo-N-(2-bromoethyl)-, hydrobromide (1:1)

Product 1

HCID 156761211-(2-Fluoro-6-methoxyphenyl)piperazineYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

2-Fluoro-6-methoxyaniline (7.80 g) and 17.23 g of di-(2-bromoethyl)amine hydrobromide were dissolved in 5 ml of water and, by heating at about 110° C. on a bath, 10 ml of 30% potassium hydroxide solution was added thereto (each about 3.5 ml once an hour). Heating was further continued (7 hours in total). After cooled, the reaction solution was made alkaline with aqueous solution of sodium hydroxide to salt out and extracted with chloroform twice. The extract was washed with saturated sodium chloride solution, dried over sodium sulfate, the solvent was evaporated therefrom, and the residue was purified by a column chromatography to give 8.95 g of oily 1-(2-fluoro-6-methoxyphenyl)piperazine in 34.93 g yield or 94%.

Workup

  1. customeach about 3.5 ml once an hour
  2. temperatureHeating
  3. custom(7 hours in total)
  4. temperatureAfter cooled
  5. extractionextracted with chloroform twice
  6. washThe extract was washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was evaporated
  9. customthe residue was purified by a column chromatography

Sources & evidence

ORD record
ord-4221356c531047a2a9f8568c1e0db29d
Source dataset
uspto-grants-1992_02
Patent number
US05086049

Linked notes

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