Butylamine → Terbinafine Hydrochloride

HRID 1648616

Reaktionsgleichung

Reaktionsgleichung von HRID 1648616
[Cl:1]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH3:17])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.C(N)CCC.[C:23]([C:27]#[CH:28])([CH3:26])([CH3:25])[CH3:24]>[Cu]I.O1CCCC1>[ClH:1].[CH3:24][C:23]([CH3:26])([CH3:25])[C:27]#[C:28]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH3:17])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 8007ButylamineHCID 135123,3-Dimethyl-1-butyneHCID 9834733(E)-3-Chloro-N-methyl-N-(1-naphthylmethyl)-2-propen-1-amine

Produkt 1

HCID 5282481Terbinafine HydrochlorideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 33 ml of tetrahydrofuran were added 5.40 g (22 mmol) of (E)-N-(3-chloro-2-propenyl)-N-methyl-1-naphthalenemethanamine, 210 mg (1.1 mmol) of copper (I) iodide and 356 mg (0.31 mmoi) of tetrakis (triphenylphospnine)palladium, and further, 4.35 ml (44 mmol) of n-butylamine and 2.83 mt (23.1 mmol) of tert-butylacetylene under ice cooling. The mixture was stirred for 17 hours at room.temperature. The reaction mixture was concentrated and the residue was subjected silica gel chromatography (n-hexane→n-hexane/ethyl acetate =9/1→4/1). The desired fractions were put together and concentrated under reduced pressure. The oily residue was dissolved in 6 ml of ethanol and 6 ml 23% hydrogen chloride methanol solution was added thereto. The solvent and excess hydrogen chloride were distilled off. The resulting crystals were suspended in diisopropyl ether, filtered, washed with diisopropyl ether and dried to obtain 6.41 g (yield: 89%) of the above identified compound as white crystalline powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe oily residue was dissolved in 6 ml of ethanol
  4. addition6 ml 23% hydrogen chloride methanol solution was added
  5. distillationThe solvent and excess hydrogen chloride were distilled off
  6. filtrationfiltered
  7. washwashed with diisopropyl ether
  8. customdried
  9. customto obtain 6.41 g (yield: 89%) of the

Quellen und Nachweise

ORD-Eintrag
ord-5166ee26c1ed46ebb9e5891c73eb1aab
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05436354

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