Triethylamine → 1-(3-methoxybenzyl)piperazine

HRID 1792503Notes

Reaction equation

HRID 1792503 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Cl.C([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)(OC(C)(C)C)=O.C(N(CC)CC)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 699943-Methoxybenzyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 4282851-(3-methoxybenzyl)piperazineYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.0 g 3-methoxy benzylchloride, 2.9 g 1-Boc piperazine, 5 mL triethylamine, and 20 mL tetrahydrofuran was stirred at room temperature for 20 minutes. The mixture was concentrated, and the residue was added to 20 mL trifluoroacetic acid and stirred at room temperature for 20 minutes. The trifluoroacetic acid was evaporated, and the residue was suspended in methanol and neutralized with an aqueous saturated sodium bicarbonate solution. The solvent was evaporated, and the residue was suspended in dichloromethane and purified by NH silica gel chromatography to give 2.4 g of the title compound as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was added to 20 mL trifluoroacetic acid
  3. stirringstirred at room temperature for 20 minutes
  4. customThe trifluoroacetic acid was evaporated
  5. customThe solvent was evaporated
  6. custompurified by NH silica gel chromatography

Sources & evidence

ORD record
ord-170f2caf988e4501a2abbd5de84e3884
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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