Hydrochloric Acid → 3'-(Benzyloxy)-2-isopropylamino-acetophenone hydrochloride

HRID 580679

Reaktionsgleichung

Reaktionsgleichung von HRID 580679
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12](=[O:15])[CH2:13]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]([NH2:22])([CH3:21])[CH3:20].[ClH:23].O>C(O)C>[ClH:23].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:12](=[O:15])[CH2:13][NH:22][CH:19]([CH3:21])[CH3:20])[CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6363IsopropylamineHCID 880311-(3-(Benzyloxy)phenyl)-2-bromoethanone

Produkt 1

HCID 201344613'-(Benzyloxy)-2-isopropylamino-acetophenone hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In 425 ml of ethanol, 64 g of 3-benzyloxyphenacyl bromide and 212 ml of iso-propylamine are stirred at 5° C. under N2 atmosphere, and the temperature is allowed to rise to 12° C. After 0.75 minutes, the clear solution is poured into 2 liters of crushed ice containing 500 ml of concentrated HCl and 1.5 liters of H2O. The mixture is stirred for 20 minutes, filtered and the solid is washed with water to afford 3'-(benzyloxy)-2-isopropylamino-acetophenone hydrochloride, mp 213°-215° C. dec. A 5 g.-sample of this material is stirred in 50 ml of methanol, and the mixture is cooled in ice and neutralized with 10% NaOH until a clear solution is obtained. To this solution, 2 g of NaBH4 is added and after 0.75 hours of stirring, the mixture is evaporated in vacuo, and the resulting solid is collected and washed with H2O. This gives, after drying, 4.4 g of m-(benzyloxy)-α-[(isopropylamino)methyl]benzyl alcohol, mp 83°-85° C.

Aufarbeitung

  1. customto rise to 12° C
  2. filtrationfiltered
  3. washthe solid is washed with water

Quellen und Nachweise

ORD-Eintrag
ord-dac4f82f13ee4bc5af6da789bfd84f80
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04754047

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