1-(2-Hydroxyethyl)piperazine → HCID 4742800, compound

HRID 1197511Notes

Reaction equation

HRID 1197511 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][CH2:18][O:19][CH:20]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.C(#N)C>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH:20]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[O:19][CH2:18][CH2:17][N:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 107793021-[Bis(4-fluorophenyl)methoxy]-2-chloroethane

Product 1

HCID 4742800HCID 4742800, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 6342AcetonitrileSolvent

Procedure

To a refluxing mixture of 1.05 g (0.0081 mol) N-(2-hydroxy-ethyl)piperazine, 0.75 g (0.0054 mol) dry potassium carbonate and 5 ml toluene, a solution of 0.76 g (0.0027 mol) 1-[(2-chloroethoxy)(4-fluorophenyl)methyl]-4-fluorobenzene in 3 ml toluene was added dropwise. The reaction mixture was refluxed for 11 h and then cooled to room temperature. It was diluted with toluene (100 ml) and extracted with 2N hydrochloric acid (100 ml). The acidic extract was washed with one portion of toluene, then rendered basic by addition of 4N sodium hydroxide solution (75 ml) and extracted with toluene (100 ml). The toluene solution was washed successively with two portions of water and once with brine. Evaporation in vacuo gave a yellowish oil, which was redissolved in acetonitrile (20 ml). The title compound was precipitated as the dimaleate salt with an excess of a maleic acid solution in acetonitrile. By recrystallization from hot acetonitrile/methanol 1.29 g (78% of the theoretical yield) of the title compound was obtained as white crystals, m.p. 163° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 11 h
  2. extractionextracted with 2N hydrochloric acid (100 ml)
  3. extractionThe acidic extract
  4. washwas washed with one portion of toluene
  5. additionrendered basic by addition of 4N sodium hydroxide solution (75 ml)
  6. extractionextracted with toluene (100 ml)
  7. washThe toluene solution was washed successively with two portions of water and once with brine
  8. customEvaporation in vacuo
  9. customgave a yellowish oil, which
  10. customThe title compound was precipitated as the dimaleate salt with an excess of a maleic acid solution in acetonitrile
  11. customBy recrystallization from hot acetonitrile/methanol 1.29 g (78% of the

Sources & evidence

ORD record
ord-66cfb3a1a04a4f188ac631877f7e6c24
Source dataset
uspto-grants-1994_01
Patent number
US05276035

Reaction notes

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