Hydrochloric Acid → 4-[[4-(2-Tolyl)-1-piperazinyl]methyl]phenylacetic acid hydrochloride

HRID 481301Notes

Reaction equation

HRID 481301 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12]C)=[O:11])=[CH:5][CH:4]=1.[ClH:14].[C:15]1([CH3:27])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(CC)CC)C.Cl>O1CCOCC1>[ClH:14].[C:15]1([CH3:27])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:22][CH2:23][N:24]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=2)[CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetateHCID 122278951-(o-Tolyl)piperazine Hydrochloride

Product 1

HCID 676807994-[[4-(2-Tolyl)-1-piperazinyl]methyl]phenylacetic acid hydrochlorideYield 52.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using 2.2 g of methyl 4-bromomethylphenylacetate, 1.9 g of 1-(2-tolyl)piperazine hydrochloride, 2.5 ml of triethylamine, and 80 ml of dioxane, the reaction procedure of Example 2 was otherwise repeated and the reaction product was converted to the hydrochloride using 2N-hydrochloric acid and recrystallized from ethanol-ether to provide 1.7 g of the title compound melting at 249° C.-252° C.

Workup

  1. customthe reaction procedure of Example 2
  2. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-43daba68db954e8791cba67c0dd6fdfe
Source dataset
uspto-grants-1998_08
Patent number
US05789409

Reaction notes

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