Hydrochloric Acid → 4-(1-Aminoethyl)benzoic acid

HRID 21780

Reaktionsgleichung

Reaktionsgleichung von HRID 21780
C([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH3:12])=[CH:7][CH:6]=1)C.C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+].Cl>CO>[C:4]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH2:21])[CH3:12])=[CH:7][CH:6]=1)([OH:3])=[O:14]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 600911Ethyl 4-acetylbenzoateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 125682714-(1-Aminoethyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

10 g of 4-acetylbenzoic acid ethyl ester and 40 g of ammonium acetate are dissolved in 210 ml of absolute methanol, and 3.63 g of sodium cyanoborohydride are added. The reaction solution is stirred for 24 hours at room temperature, cooled to 4° and adjusted to a pH of 1 by the addition of concentrated hydrochloric acid. The methanol is removed under reduced pressure and the suspension that remains is filtered. The aqueous tiltrate is washed with diethyl ether, adjusted to a pH of 10 at 4° by the addition of solid sodium hydroxide and extracted with diethyl ether. Drying is carried out over sodium sulfate and is followed by concentration to dryness by evaporation under reduced pressure, and the oil that remains is distilled under reduced pressure to give 1-(4-carboxyphenyl)ethylamine having a boiling point of 130°-140° (6×10-2 mbar).

Aufarbeitung

  1. temperaturecooled to 4°
  2. customThe methanol is removed under reduced pressure
  3. filtrationthe suspension that remains is filtered
  4. washThe aqueous tiltrate is washed with diethyl ether
  5. additionadjusted to a pH of 10 at 4° by the addition of solid sodium hydroxide
  6. extractionextracted with diethyl ether
  7. customDrying
  8. concentrationis followed by concentration to dryness by evaporation under reduced pressure
  9. distillationthe oil that remains is distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-acf3d7a93d8141a684d01a171fb0a631
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424441

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