Diisopropylethylamine → HCID 54018480, Verbindung

HRID 1762582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1762582
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:13]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:10]2)=[CH:5][CH:4]=1.Br.[CH3:26][O:27][C:28]([C:30]1[CH2:31][NH:32][CH2:33][CH2:34][CH:35]=1)=[O:29].C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:26][O:27][C:28]([C:30]1[CH2:31][N:32]([CH2:13][CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:10]2)[CH2:33][CH2:34][CH:35]=1)=[O:29]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 11210176p-Toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) esterHCID 15560296Guvacoline Hydrobromide

Produkt 1

HCID 54018480HCID 54018480, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5.19 g (15 mmol) of p-toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester in 75 ml of dimethylformamide there are added first 3.66 g (16.5 mmol) of 1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester hydrobromide (guvacoline hydrobromide) and then 6.78 g (52.5 mmol) of N-ethyl-N,N-diisopropylamine. The mixture is stirred at 60° for 18 hours and then concentrated by evaporation under a high vacuum. Water is added to the residue and extraction is carried out with diethyl ether. The organic phases are washed with water and extracted with 2N hydrochloric acid. The hydrochloric acid extracts are rendered alkaline at reduced temperature with sodium hydroxide solution (30%) and are extracted with dichloromethane, whereupon the combined organic phases are dried over sodium sulphate and concentrated by evaporation under reduced pressure. 1-[(7-methoxy-1,2,3,4-tetrahydro-naphth-2-yl)methyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester is obtained in the form of a light-yellow oil.

Aufarbeitung

  1. concentrationconcentrated by evaporation under a high vacuum
  2. additionWater is added to the residue and extraction
  3. washThe organic phases are washed with water
  4. extractionextracted with 2N hydrochloric acid
  5. extractionare extracted with dichloromethane, whereupon the combined organic phases
  6. dry with materialare dried over sodium sulphate
  7. concentrationconcentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7b4e084565ba4c199858617f9f949fd2
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04833169

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