Hydrochloric Acid → 1-[[2-(5-Bromo-3-indolyl)-1,1-dimethylethyl]amino]-3-(2-methylphenoxy)-2-propanol hydrochloride

HRID 224894

Reaktionsgleichung

Reaktionsgleichung von HRID 224894
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[CH2:8][O:7]1.[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:23][C:24]([CH3:27])([CH3:26])[NH2:25].[ClH:28]>C(#N)C>[ClH:28].[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:23][C:24]([NH:25][CH2:8][CH:6]([OH:7])[CH2:5][O:4][C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[CH3:1])([CH3:26])[CH3:27]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 13259Indole, 3-(2-amino-2-methylpropyl)-5-bromo-HCID 16640o-CRESYL GLYCIDYL ETHER

Produkt 1

HCID 126196531-[[2-(5-Bromo-3-indolyl)-1,1-dimethylethyl]amino]-3-(2-methylphenoxy)-2-propanol hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(2-Methylphenoxymethyl)oxirane, 4.1 g. (0.025 mole) and 6.65 g. (0.025 mole) of 5-bromo-α,α-dimethyl-1H-indol-3-yl-ethaneamine were mixed and heated at 140° for 1 hr. The mixture was then cooled and dissolved in 40 ml. of acetonitrile while still warm. The product was converted to the hydrochloride salt by treatment of the solution with 5 N ethanolic HCl. The solvent was removed by distillation and the residue dissolved in 30 ml. of acetonitrile. The product crystallized from this solution, yield 11.0 g., m.p. 197°-199°. This material was recrystallized from methanol/isopropanol, yield 8.0 g., m.p. 198.0°-200.0° dec. (corr.).

Aufarbeitung

  1. temperatureheated at 140° for 1 hr
  2. temperatureThe mixture was then cooled
  3. dissolutiondissolved in 40 ml
  4. customThe solvent was removed by distillation
  5. dissolutionthe residue dissolved in 30 ml
  6. customThe product crystallized from this solution, yield 11.0 g
  7. customThis material was recrystallized from methanol/isopropanol, yield 8.0 g

Quellen und Nachweise

ORD-Eintrag
ord-24faa05a5cf64903a1ba4521dbd3f790
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04234595

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