Triethylamine → HCID 69246465, compound

HRID 2249405Notes

Reaction equation

HRID 2249405 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:15][O:16][C:17]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1)=[O:18]>Cl>[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[CH2:23][C:22]1[CH:21]=[CH:20][C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 69246465HCID 69246465, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of N-methyl piperazine (80 g, 0.91 mol) and triethylamine (232 g, 2.29 mol) in absolute alcohol (1750 ml) was added dropwise at 0° C. a solution of 4-methoxycarbonyl-benzyl bromide (252 g, 1.1034 mol) in absolute alcohol (250 ml). The mixture was stirred overnight at RT. Then the mixture was concentrated and the residue obtained was taken up in 1.5N HCl (3 L) then washed with diethyl ether (3 times) and ethyl acetate. The solution was neutralized with a 10% aqueous NaOH solution and basified up to pH=8 with a 10% aqueous NaHCO3 solution. The product was extracted with CHCl3, washed with water and brine then dried over Na2SO4. The solvent was removed and the crude was purified by column chromatography CHCl3/MeOH to give N-methyl(4-methoxy carbonyl benzyl)piperazine (150 g, 70%) as a brown liquid.

Workup

  1. concentrationThen the mixture was concentrated
  2. customthe residue obtained
  3. washthen washed with diethyl ether (3 times) and ethyl acetate
  4. extractionThe product was extracted with CHCl3
  5. washwashed with water and brine
  6. dry with materialthen dried over Na2SO4
  7. customThe solvent was removed
  8. customthe crude was purified by column chromatography CHCl3/MeOH

Sources & evidence

ORD record
ord-1cc3f0d7ec474854983966035548223f
Source dataset
uspto-grants-2008_01
Patent number
US07314878B2

Reaction notes

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