Pyridine → 1-(2-Methoxyphenyl)piperazine

HRID 1251319Notes

Reaction equation

HRID 1251319 reaction equation
NCC[N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:6][CH2:5]1.N1C=CC=CC=1.BrCCC(Cl)=O>ClCCl>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:7]1[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 84944Propanoyl chloride, 3-bromo-HCID 103991861-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 13461-(2-Methoxyphenyl)piperazineYield 107.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a chilled solution (0° C.) of 4-[(2-amino)ethyl]-1-(2-methoxyphenyl)piperazine (10.46 mmol) in 40 mL of dichloromethane were added pyridine (12.55 mmol) and a solution of 3-bromopropionyl chloride (11.51 mmol) in 10 mL of dichloromethane. After addition, the reaction mixture was warmed to room temperature, and stirred for 1 hour. The reaction mixture was quenched with saturated sodium carbonate, extracted with dichloromethane. The organic phase was washed with brine, water, and dried over magnesium sulfate Filtration and evaporation of the solvents gave a residue that was purified by flash chromatography using 3-5% of methanol and 0.5% of ammonium hydroxide in ethyl acetate to give 4-[2-(3′-bromo)propionamido)ethyl]-1-(2-methoxyphenyl)piperazine (2.16 g, 56%).

Workup

  1. additionAfter addition
  2. customThe reaction mixture was quenched with saturated sodium carbonate
  3. extractionextracted with dichloromethane
  4. washThe organic phase was washed with brine, water
  5. dry with materialdried over magnesium sulfate Filtration and evaporation of the solvents
  6. customgave a residue that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-930dbffd43f349839769bf7a6eece3f3
Source dataset
uspto-grants-2002_01
Patent number
US06342498B1

Reaction notes

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