Hydrazine hydrate (1:1) → 3-(4-Benzhydryl-1-piperazinyl)-1-propanamine

HRID 1383461Notes

Reaction equation

HRID 1383461 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][N:23]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[CH:1]([N:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][CH2:22][NH2:23])[CH2:18][CH2:19]1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10928314HCID 10928314, compound

Product 1

HCID 137677783-(4-Benzhydryl-1-piperazinyl)-1-propanamineYield 42.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude 2-[3-(4-benzhydryl-piperazin-1-yl)-propyl]-isoindole-1,3-dione (930 mg) was dissolved in ethanol (2 ml), followed by the addition of hydrazine hydrate (large excess, 2-3 ml). The solution was stirred at room temperature overnight. The white solid was precipitated. The white solid was filtered off and washed with small amount of ethanol. The filtrates were combined and concentrated. The resulted residue was dissolved in toluene (100 ml). The solution was washed with water (3×15 ml) and dried over anhydrous Na2SO4. After evaporated the solvent, the crude product 3-(4-benzhydryl-piperazin-1-yl)-propylamine was obtained (276 mg, 42.7% yield).

Workup

  1. customThe white solid was precipitated
  2. filtrationThe white solid was filtered off
  3. washwashed with small amount of ethanol
  4. concentrationconcentrated
  5. dissolutionThe resulted residue was dissolved in toluene (100 ml)
  6. washThe solution was washed with water (3×15 ml)
  7. dry with materialdried over anhydrous Na2SO4
  8. customAfter evaporated the solvent

Sources & evidence

ORD record
ord-e4237cf737044ba88183d42bd4b01aa1
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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