Propylhexedrine → {2-[(2-Cyclohexyl-1-methylethyl)methylamino]-2-oxoethoxy}acetic Acid

HRID 2049443

Reaktionsgleichung

Reaktionsgleichung von HRID 2049443
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][O:3][CH2:2]1.[CH3:9][CH:10]([NH:18][CH3:19])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>ClCCl>[CH:12]1([CH2:11][CH:10]([N:18]([CH3:19])[C:5](=[O:6])[CH2:4][O:3][CH2:2][C:1]([OH:7])=[O:8])[CH3:9])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

4

Edukt 2

HCID 7558PropylhexedrineHCID 782321,4-Dioxane-2,6-dione

Produkt 1

HCID 12796199{2-[(2-Cyclohexyl-1-methylethyl)methylamino]-2-oxoethoxy}acetic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of 11.63 grams (0.100 mole) of diglycolic anhydride in 1 liter of dichloromethane (prepared by heating the anhydride and dichloromethane on a steam bath) was added to a solution of 15.55 grams (0.100 mole) of propylhexedrine in 700 milliliters of dichloromethane at temperatures in the range of from about 21° to about 30° during an interval of about 10 minutes. After the addition, the mixture was stirred at a temperature range of 25° to 30° C. for about 40 minutes whereupon a reaction took place with the formation of a product in the reaction mixture. The mixture was then concentrated on a rotary evaporator to recover the {2-[(2-cyclohexyl-1-methylethyl)methylamino]-2-oxoethoxy}-acetic acid product as a partially crystalline residue which after recrystallization from an ethyl acetate-hexane mixture was in the form of white plates, m.p. 90°-91° C.

Aufarbeitung

  1. additionAfter the addition
  2. concentrationThe mixture was then concentrated on a rotary evaporator
  3. customto recover the {2-[(2-cyclohexyl-1-methylethyl)methylamino]-2-oxoethoxy}-acetic acid product as a partially crystalline residue which
  4. customafter recrystallization from an ethyl acetate-hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-c2706f1c204d48bd84695cb382e07cb6
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04197315

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