Hydrochloric Acid → N-[2-(4-(2-Methylaminoethoxy)phenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

HRID 477144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477144
[CH3:1][NH:2][C:3]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([OH:28])[C:19]2[N:20]=[C:21]([C:24]([F:27])([F:26])[F:25])[S:22][CH:23]=2)[CH3:15])=[CH:9][CH:8]=1)=O.CO.Cl>O1CCCC1>[CH3:1][NH:2][CH2:3][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([OH:28])[C:19]2[N:20]=[C:21]([C:24]([F:25])([F:27])[F:26])[S:22][CH:23]=2)[CH3:15])=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 19974232N-[2-(4-methylaminocarbonylmethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

Produkt 1

HCID 19974228N-[2-(4-(2-Methylaminoethoxy)phenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.2 ml of borane/dimethyl sulfide complex are added to a solution of 0.38 g of N-[2-(4-methylaminocarbonylmethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine in 20 ml of absolute tetrahydrofuran, and the mixture is heated to reflux for three hours. The 4 ml of methanol are cautiously added dropwise to the reaction mixture, and the mixture is heated to reflux for one hour. After cooling to room temperature, ethereal hydrochloric acid is added. The resulting solution is evaporated, the resulting residue is taken up in 15 ml of water, and the solution is made alkaline with concentrated ammonia and extracted several times with methylene chloride. The combined extracts are dried with sodium sulphate, evaporated and purified on a silica gel column using methylene chloride/methanol=8:2 as eluant.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureto reflux for three hours
  3. temperaturethe mixture is heated
  4. temperatureto reflux for one hour
  5. customThe resulting solution is evaporated
  6. extractionextracted several times with methylene chloride
  7. dry with materialThe combined extracts are dried with sodium sulphate
  8. customevaporated
  9. custompurified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-98b2fbd3537444a8b6d981bc316d7c8d
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886814

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