Hydrazine hydrate (1:1) → 2-[4-(2-aminoethyl)piperazin-1-yl]ethanol

HRID 555708Notes

Reaction equation

HRID 555708 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:6][CH2:5]1.O.NN>CCO>[NH2:12][CH2:11][CH2:10][N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66986846HCID 66986846, compound

Product 1

HCID 47424572-[4-(2-aminoethyl)piperazin-1-yl]ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-{2-[4-(2-Hydroxy-ethyl)-piperazin-1-yl]-ethyl}-isoindole-1,3-dione (370 mg, 1.2 mmol) is dissolved in EtOH (8 mL) and hydrazine hydrate (88 mL, 1.8 mmol) is added at RT. The reaction mixture is then refluxed for 3 h and allowed to cool to RT again. The precipitated product is isolated by filtration, washed subsequently with cold EtOH and dried in HV to give the title compound as a white powder. ES-MS: M+H=174.2. 1HNMR (MeOH-d4) δ 4.24 (bs, 2H), 3.41 (t, 2H), 2.62 (t, 2H), 2.54-2.50 (m, 2H), 2-39-2.201 (m, 10H).

Workup

  1. temperatureThe reaction mixture is then refluxed for 3 h
  2. customThe precipitated product is isolated by filtration
  3. washwashed subsequently with cold EtOH
  4. customdried in HV

Sources & evidence

ORD record
ord-696d9252b002456aa357292bbb20d753
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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