Water → 1-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazine

HRID 1251318Notes

Reaction equation

HRID 1251318 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2C(=O)C3=CC=CC=C3C2=O)[CH2:11][CH2:10]1.O.NN.O>C(O)C>[NH2:17][CH2:16][CH2:15][N:12]1[CH2:11][CH2:10][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 86874532-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]isoindole-1,3-dione

Product 1

HCID 103991861-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazineYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-(2-methoxyphenyl)-4-[(2-phthalimido)-ethyl] piperazine (23.4 mmol) in 160 mL of ethanol were added hydrazine hydrate (31 mL) and water (40 mL) The mixture was stirred at room temperature for 18 hours. The volatiles were evaporated. The residue was partitioned between ethyl acetate and saturated potassium carbonate solution. The organic layer was washed with brine and water, dried over magnesium sulfate, filtered and concentrated to give 4-[(2-amino)ethyl]-1-(2-methoxyphenyl)piperazine (5.45 g, 99%).

Workup

  1. customThe volatiles were evaporated
  2. customThe residue was partitioned between ethyl acetate and saturated potassium carbonate solution
  3. washThe organic layer was washed with brine and water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7f3ba7819367411f90f3c85be5c489d6
Source dataset
uspto-grants-2002_01
Patent number
US06342498B1

Reaction notes

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