N-Methylbenzylamine → 3-(N-benzyl-N-methylamino)methyl-5-cyanomethyl-1,2,4-oxadiazole

HRID 247120

Reaktionsgleichung

Reaktionsgleichung von HRID 247120
C1C2[CH:6]([C:8]3[O:12][N:11]=[C:10](N)[N:9]=3)[CH2:7][N:3](C2)C1.[CH3:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:23](N(CC)CC)C>C1COCC1>[CH2:16]([N:15]([CH2:23][C:10]1[N:9]=[C:8]([CH2:6][C:7]#[N:3])[O:12][N:11]=1)[CH3:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 1639383-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptane

Produkt 1

HCID 201612213-(N-benzyl-N-methylamino)methyl-5-cyanomethyl-1,2,4-oxadiazoleAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of 8.0 g of the oxadiazole prepared above, 9.26 g of N-methylbenzylamine and 10.32 g of triethylamine in 50 ml of THF was allowed to stand at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The resultant solution was washed with water, dried and evaporated in vacuo. The residue was chromatographed on silica gel using benzeneethyl acetate (2:1) as eluent to give 5.56 g of 3-(N-benzyl-N-methylamino)methyl-5-cyanomethyl-1,2,4-oxadiazole as an oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe resultant solution was washed with water
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel using benzeneethyl acetate (2:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-d472f0b3857543bf941249551c0b37ea
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705786

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