Hydrazine hydrate (1:1) → HCID 21993633, compound

HRID 1978390Notes

Reaction equation

HRID 1978390 reaction equation
O.NN.[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]2C(=O)C3=CC=CC=C3C2=O)[C:13](=[O:31])[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(O)C>[NH2:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][N:11]([C:9]([O:8][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:10])[CH2:12][C:13]1=[O:31]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 219938971,1-Dimethylethyl 4-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]-3-oxo-1-piperazinecarboxylate

Product 1

HCID 21993633HCID 21993633, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (1.75 g, 46.6 mmol) was added to a stirred solution of 4-tert-butoxycarbonyl-1-(3-phthalimidopropan-1-yl)-2-oxopiperazine (9.02 g, 23.3 mmol) in ethanol (50 ml) at room temperature. The reaction mixture was refluxed for 1 hour. The precipitates were removed off by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in 2N-sodium hydroxide and extracted with chloroform. The extract was washed with brine, dried over MgSO4 and concentrated in vacuo to give 1-(3-aminopropan-1-yl)-4-tert-butoxycarbonyl-2-oxopiperazine as a colorless oil (5.43 g, 91%).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. customThe precipitates were removed off by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in 2N-sodium hydroxide
  5. extractionextracted with chloroform
  6. washThe extract was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd4856eb692642e2a8934bd7a6dc2052
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

Loading…