Triethylamine → Benzeneacetamide, N-(2-(2,3-dihydro-6-methyl-1H-inden-5-yl)ethyl)-3,4-dimethoxy-

HRID 224331

Reaktionsgleichung

Reaktionsgleichung von HRID 224331
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[CH3:13])[CH2:9][CH2:8][CH2:7]2.C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:31][C:32](Cl)=[O:33])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]>C1C=CC=CC=1>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:31][C:32]([NH:1][CH2:2][CH2:3][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][C:12]=2[CH3:13])[CH2:9][CH2:8][CH2:7]3)=[O:33])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 3604458(3,4-Dimethoxyphenyl)acetyl chlorideHCID 124261245-Aminoethyl-6-methylindan

Produkt 1

HCID 3051196Benzeneacetamide, N-(2-(2,3-dihydro-6-methyl-1H-inden-5-yl)ethyl)-3,4-dimethoxy-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

5-Aminoethyl-6-methylindan (4.0 g, 0.029 mole) was dissolved in 100 ml of dry benzene, 4 ml of triethylamine was added and a solution of the previously prepared 3,4-dimethoxyphenylacetyl chloride in dry benzene was added to the substituted indan mixture. The reaction mixture was refluxed for several hours and then gently heated overnight at a temperature below reflux. The reaction was then cooled, washed with 3×100 ml of 20% HCl solution, 3×100 ml of 8% NaHCO3 solution and 2×125 ml of water. The benzene layer was then reduced in volume on a rotary evaporator to yield a solid precipitate. The solid was filtered, washed with benzene, air dried to yield a slightly pink powder (3.5 g, mp 144°-145° C.). The crude product was then recrystallized from benzene (large volume), mp 144°-144.5° C.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for several hours
  2. temperaturegently heated overnight at a temperature below reflux
  3. temperatureThe reaction was then cooled
  4. washwashed with 3×100 ml of 20% HCl solution, 3×100 ml of 8% NaHCO3 solution and 2×125 ml of water
  5. customThe benzene layer was then reduced in volume on a rotary evaporator
  6. customto yield a solid precipitate
  7. filtrationThe solid was filtered
  8. washwashed with benzene, air
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-663cc495f71a4c84924194f9d7641ca3
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04232014

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