Hydrochloric Acid → (E)-N,N-diethyl-1,4-diaminobut-2-ene dihydrochloride

HRID 1449649Notes

Reaction equation

HRID 1449649 reaction equation
[C:1]1(=O)[N:5]([CH2:6]/[CH:7]=C/CBr)[C:4](=O)[C:3]2=[CH:12][CH:13]=CC=[C:2]12.C([NH:19]CC)C.[F-].[K+].[ClH:24]>C(#N)C.C(O)(=O)C>[ClH:24].[ClH:24].[CH2:1]([N:5]([CH2:6][CH3:7])[CH2:4]/[CH:3]=[CH:12]/[CH2:13][NH2:19])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 522689Potassium FluorideHCID 105168412-(4-Bromobut-2-en-1-yl)isoindoline-1,3-dione

Product 1

HCID 23352203(E)-N,N-diethyl-1,4-diaminobut-2-ene dihydrochlorideYield 41%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

(E)-1-Phthalimido-4-bromobut-2-ene (4.2 g, 15 mmol), diethylamine (1.1 g, 15 mmol) and KF supported on Celite (7.5 g) were stirred together in acetonitrile (75 ml) at 40° C. for 18 h. The solution was filtered, and the filtrate was concentrated in vacuo to afford an oil, which was dissolved in glacial acetic acid (30 ml) and conc. HCl (30 ml). The mixture was heated at reflux for 30 h. The solution was cooled, filtered and the solvents were removed in vacuo to afford (E)-N,N-diethyl-1,4-diaminobut-2-ene dihydrochloride as an oil (1.32 g, 41%). δH (90 MHz, D2O) 1.19 (6H, m) 3.24 (4H, q), 4.05 (4H, m) and 5.96 (2H, m).

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto afford an oil, which
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 30 h
  6. temperatureThe solution was cooled
  7. filtrationfiltered
  8. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-7f19bd30dab849c0b8e40129287258e8
Source dataset
uspto-grants-1997_02
Patent number
US05599847

Reaction notes

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