Hydrochloric Acid → HCID 18757069, compound

HRID 434110Notes

Reaction equation

HRID 434110 reaction equation
O.NN.[CH2:4]([N:11]([CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1C(=O)C2=CC=CC=C2C1=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>C(O)C.CCOCC>[CH2:4]([N:11]([CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 18757066HCID 18757066, compound

Product 1

HCID 18757069HCID 18757069, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of hydrazine hydrate solution (0.83 ml, 0.017 mole) in ethanol (20 ml) is added to a solution of N-[4-{benzyl[2-(2-methoxyphenoxy)ethyl]amino}butyl]phthalimide (7.2 g, 0.016 mole) in ethanol (70 ml), the solution is stirred and heated to reflux for 3 hours. After cooling to ambient temperature, the solvent is evaporated at reduced pressure and the residual oil is treated with 1 N hydrochloric acid (40 ml). The precipitate formed is removed by filtration, washed in water, and the filtrate and the washing liquids are made basic with potassium carbonate (16 g). The separated oil is extracted with dichloromethane (3×80 ml) and the extracts dried over magnesium sulfate. Filtration and evaporation of the solvent at reduced pressure yields 4.4 g (86%) of the theoretical yield in the form of an oil. The treatment of an etherized solution of the free base with a saturated solution of hydrogen chloride gas in ether makes it possible to obtain N-benzyl-N-[2-(2-methoxyphenoxy)ethyl]-1,4-butanediamine as a dihydrochlorated salt; mp 200-202 degrees C. after recrystallization from ethanol.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customthe solvent is evaporated at reduced pressure
  4. additionthe residual oil is treated with 1 N hydrochloric acid (40 ml)
  5. customThe precipitate formed
  6. customis removed by filtration
  7. washwashed in water
  8. extractionThe separated oil is extracted with dichloromethane (3×80 ml)
  9. dry with materialthe extracts dried over magnesium sulfate
  10. filtrationFiltration and evaporation of the solvent at reduced pressure
  11. customyields 4.4 g (86%) of the
  12. customtheoretical yield in the form of an oil

Sources & evidence

ORD record
ord-4f23e89b690c46a197fb2a61ca1f7efc
Source dataset
uspto-grants-2003_12
Patent number
US06670400B1

Reaction notes

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