Triethylamine → HCID 18357078, compound

HRID 346671Notes

Reaction equation

HRID 346671 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1>C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:21][C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 705171-(4-Pyridyl)piperazineHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 18357078HCID 18357078, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-(4-pyridyl)piperazine (13.1 g) in ethyl acetate (200 ml) was added triethylamine (56 ml) followed dropwise, over 5 hours, by a solution of methyl 4-bromomethylbenzoate (18.41 g). The mixture was stirred at room temperature for 18 hours. The mixture was partitioned between water and ethyl acetate. The organic extracts were dried (MgSO4) and evaporated to give a gum, which was purified by column chromatograhy on silica eluting with increasing concentrations of methanol/dichloromethane to give methyl 4-(4-(4-pyridyl)piperazin-1-ylmethyl)benzoate (13.1 g) as a solid;

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. customevaporated
  4. customto give a gum, which
  5. customwas purified by column chromatograhy on silica eluting
  6. temperaturewith increasing concentrations of methanol/dichloromethane

Sources & evidence

ORD record
ord-db977430327c4979b9e1d5e7ba78624e
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Reaction notes

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