Triethylamine → N,N-diethyl-N'-(2,3-dihydro-6-methoxy-2-methyl-4-benzofuranyl)-1,2-ethanediamine dihydrochloride

HRID 614008Notes

Reaction equation

HRID 614008 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][Cl:6])[CH3:2].[K].[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[O:18][CH:17]([CH3:19])[CH2:16][C:15]2=[C:20]([NH2:22])[CH:21]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[ClH:6].[ClH:6].[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:22][C:20]1[C:15]2[CH2:16][CH:17]([CH3:19])[O:18][C:14]=2[CH:13]=[C:12]([O:11][CH3:10])[CH:21]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13364Diethylaminoethyl chlorideHCID 5462222PotassiumHCID 213298112,3-Dihydro-6-methoxy-2-methyl-4-benzofuranamine

Product 1

HCID 21329798N,N-diethyl-N'-(2,3-dihydro-6-methoxy-2-methyl-4-benzofuranyl)-1,2-ethanediamine dihydrochlorideYield 97.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.80 grams of 2-diethylamino-ethyl chloride and traces of potassium jodide are added to a solution of 3 grams of 2,3-dihydro-6-methoxy-2-methyl-4-benzofuranamine and 2.02 grams of triethylamine in 50 cc of anhydrous toluene and the resulting reaction mixture is refluxed for 16 hours. After cooling and washing with water, the toluene phase is dried over Na2SO4 and then concentrated to dryness. Hydrochloric acid is added to an ether solution of the resulting oily residue until a solid precipitates then the mixture is cooled. The precipitate is recovered on filter and recrystallized from ethanol by addition of ethyl ether, yielding 3.55 grams of the title compound. M.p. 158°-159° C.

Workup

  1. customthe resulting reaction mixture
  2. temperatureis refluxed for 16 hours
  3. temperatureAfter cooling
  4. washwashing with water
  5. dry with materialthe toluene phase is dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. additionHydrochloric acid is added to an ether solution of the resulting oily residue until a solid
  8. customprecipitates
  9. temperaturethe mixture is cooled
  10. customThe precipitate is recovered
  11. filtrationon filter
  12. customrecrystallized from ethanol by addition of ethyl ether

Sources & evidence

ORD record
ord-fc823c00d5df413ab68ff840184cb85a
Source dataset
uspto-grants-1979_03
Patent number
US04143055

Reaction notes

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