Triethylamine → Methyl 4-[(4-diphenylmethyl-1-piperazinyl)methyl]phenylacetate

HRID 481297

Reaction equation

HRID 481297 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.[CH:14]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>O1CCOCC1>[C:21]1([CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:27]2[CH2:28][CH2:29][N:30]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=3)[CH2:31][CH2:32]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70048BenzhydrylpiperazineHCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetate

Product 1

HCID 10993378Methyl 4-[(4-diphenylmethyl-1-piperazinyl)methyl]phenylacetateYield 90.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 200 ml eggplant-shaped flask was charged with 5.38 g of methyl 4-bromomethylphenylacetate, 6.06 g of 1-benzhydrylpiperazine, 6.1 ml of triethylamine, and 100 ml of dioxane and the mixture was stirred at room temperature for 5 hours. The solvent was then distilled off and the residue was extracted with ethyl acetate. The extract was washed with water, the solvent was distilled off, and the residue was recrystallized from methanol to provide 8.33 g of methyl 4-[(4-diphenylmethyl-1-piperazinyl)methyl]phenylacetate melting at 124° C.-125° C.

Workup

  1. distillationThe solvent was then distilled off
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. distillationthe solvent was distilled off
  5. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-89b68ced720c466195934876f641ea89
Source dataset
uspto-grants-1998_08
Patent number
US05789409

Linked notes

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