Triethylamine → HCID 66559586, compound

HRID 1750135Notes

Reaction equation

HRID 1750135 reaction equation
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][CH:18]=1.C(N(CC)CC)C>CC#N.O>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:13]2[CH2:14][CH2:15][N:10]([C:4]3[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:3]=3[Cl:2])[CH2:11][CH2:12]2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochloride

Product 1

HCID 66559586HCID 66559586, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of intermediate 41 (294 mg, 1.1 mmol), 1-bromo-4-(bromomethyl)benzene (250 mg, 1.0 mmol) and anhydrous triethylamine (253 mg, 2.5 mmol) was dissolved in CH3CN and the solution was heated to reflux for 4 h. The solution was diluted with water and extracted with EtOAc. The combined organic layers were washed with saturated aq NaHCO3, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE/EtOAc=8:1) to give 1-(4-bromobenzyl)-4-(2,3-dichlorophenyl)piperazine (intermediate 54) (220 mg, 74%) as a white solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 4 h
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with saturated aq NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel column (elution with PE/EtOAc=8:1)

Sources & evidence

ORD record
ord-996c75a572ba4f7d98b6b202b4d1707f
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

Loading…