3-Chloropropyl(diethyl)amine → HCID 68143942, compound

HRID 1606587Notes

Reaction equation

HRID 1606587 reaction equation
[O:1]=[C:2]1[O:7][C:6]2[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=[CH:11][C:5]=2[C:4]2[CH:15]=[CH:16][C:17]([C:19]([OH:21])=[O:20])=[CH:18][C:3]1=2.[CH2:22]([N:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][Cl:28])[CH3:23]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(O)(C)C>[ClH:28].[ClH:28].[CH2:22]([N:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][O:13][C:12]([C:9]1[CH:10]=[CH:11][C:5]2[C:4]3[CH:15]=[CH:16][C:17]([C:19]([O:21][CH2:27][CH2:26][CH2:25][N:24]([CH2:29][CH3:30])[CH2:22][CH3:23])=[O:20])=[CH:18][C:3]=3[C:2](=[O:1])[O:7][C:6]=2[CH:8]=1)=[O:14])[CH3:23]

Participants

5

Reactant 2

HCID 669183-Chloropropyl(diethyl)amineHCID 21543589HCID 21543589, compound

Product 1

HCID 68143942HCID 68143942, compound

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 11.0 g (0.04 mole) of 6-oxo-6H-dibenzo [b,d]pyran-3,8-dicarboxylic acid, 18.0 g (0.12 mole) of γ-diethylaminopropyl chloride and 400 ml of isopropyl alcohol are stirred and heated to its reflux temperature. A catalytic amount of benzyltrimethylammonium chloride, 0.3 ml of a 60% aqueous solution, is added and the reaction mixture heated to reflux for an additional 24 hours. On cooling, the reaction mixture is filtered, and the residue washed with isopropyl alcohol. This product is dissolved in boiling ethanol, treated with charcoal, filtered and cooled to room temperature. After standing for 1 hour, the gelatinous precipitate which appears is filtered and the filtrate cooled to -20° C. The product which forms is filtered, washed with ethanol and again recrystallized from ethanol to yield the desired bis[3-(diethylamino) propyl]6-oxo-6H-dibenzo[b,d]pyran-3,8-dicarboxylate dihydrochloride as a tan-colored solid, soluble in water and having a m.p. of 250°-1° C. (dec.) (placed in m.p. bath previously heated at 240° C.), λmax 294, and E1cm1% 464.

Workup

  1. temperatureheated to its
  2. temperaturereflux temperature
  3. temperaturethe reaction mixture heated
  4. temperatureto reflux for an additional 24 hours
  5. temperatureOn cooling
  6. filtrationthe reaction mixture is filtered
  7. washthe residue washed with isopropyl alcohol
  8. dissolutionThis product is dissolved
  9. additiontreated with charcoal
  10. filtrationfiltered
  11. filtrationthe gelatinous precipitate which appears is filtered
  12. temperaturethe filtrate cooled to -20° C
  13. filtrationThe product which forms is filtered
  14. washwashed with ethanol
  15. customagain recrystallized from ethanol

Sources & evidence

ORD record
ord-28b8fbfb500c48bb96c93c9068ff14fa
Source dataset
uspto-grants-1976_04
Patent number
US03953455

Reaction notes

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