Triethylamine → 1-(2-Chlorophenyl)-4-{2-[bis(4-hydroxyphenyl)methyl]benzyl}piperazine

HRID 36444

Reaction equation

HRID 36444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=2)[C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[CH2:31]Br)=[CH:24][CH:23]=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:31][C:30]2[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=2[CH:28]([C:25]2[CH:24]=[CH:23][C:22]([OH:21])=[CH:27][CH:26]=2)[C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4156281-(2-Chlorophenyl)piperazineHCID 199381762-[Bis(4-hydroxyphenyl)methyl]benzylbromide

Product 1

HCID 199381181-(2-Chlorophenyl)-4-{2-[bis(4-hydroxyphenyl)methyl]benzyl}piperazineYield 14.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of tetrahydrofuran were dissolved 1.5 g of 1-(2-chlorophenyl)piperazine and 5 ml of triethylamine, and 3.4 g of 2-[bis(4-hydroxyphenyl)methyl]benzylbromide was added thereto. The mixture was heated under reflux for 3.5 hours, and then insoluble substances were filtered off. The filtrate was concentrated, and the residue was subjected to extraction with the addition of water and ethyl acetate. The organic layer was separated, and the aqueous layer was then extracted with ethyl acetate. The organic layers were combined and then dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel chromatography to afford 0.54 g of the desired compound (Compound 89).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3.5 hours
  4. filtrationinsoluble substances were filtered off
  5. concentrationThe filtrate was concentrated
  6. extractionthe residue was subjected to extraction with the addition of water and ethyl acetate
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was then extracted with ethyl acetate
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated off under reduced pressure
  11. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0208c64273a84e8e8c4fda96508a2f39
Source dataset
uspto-grants-1995_05
Patent number
US05413997

Linked notes

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