Hydrochloric Acid → 1-(3-Aminopropyl)-4-methylpiperazine

HRID 1896076Notes

Reaction equation

HRID 1896076 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][N:11]2C(=O)C3=CC=CC=C3C2=O)[CH2:4][CH2:3]1.O.NN.Cl.C([O-])([O-])=O.[K+].[K+]>C(O)C.CO.C(Cl)Cl>[NH2:11][CH2:10][CH2:9][CH2:8][N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 202494272-[3-(4-Methylpiperazin-1-yl)propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 783281-(3-Aminopropyl)-4-methylpiperazineYield 39%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(3-(4-methylpiperazin-1-yl)propyl)phthalimide (6.2 g, 21.6 mM) and hydrazine monohydrate (1.13 g, 26 mM) in ethanol (60 mL) and methanol (60 mL) was refluxed for 4 hours. After cooling to room temperature, concentrated HCl (2.4 mL) was added and the mixture heated under reflux for another hour. After removing the solvent, water (100 mL) was added, the mixture stirred and insoluble material removed by filtration. Solid K2CO3 (1.2 eq) and CH2Cl2 (100 mL) was added to the aqueous layer; the mixture stirred, and was then filtered. The organic layer was washed with water (3×20 mL). The combined aqueous layers were washed with Et2O. Water was removed from the organic layers, which were then dried and evaporated to give 1-(3-aminopropyl)-4-methylpiperazine as an oil in 39% yield. 1H NMR (CDCl3): δ=1.55 (m, 2H, CH2), 2.20 (s, 3H, CH3), 2.34 (t, 2H, CH2), 2.67 (t, 2H, CH2). MS (ES+): 157.9.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for another hour
  3. customAfter removing the solvent, water (100 mL)
  4. additionwas added
  5. custominsoluble material removed by filtration
  6. stirringthe mixture stirred
  7. filtrationwas then filtered
  8. washThe organic layer was washed with water (3×20 mL)
  9. washThe combined aqueous layers were washed with Et2O
  10. customWater was removed from the organic layers, which
  11. customwere then dried
  12. customevaporated

Sources & evidence

ORD record
ord-e742e10657244f48aa1d60696110dee5
Source dataset
uspto-grants-2013_08
Patent number
US08518885B2

Reaction notes

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