Potassium Iodide → HCID 18469945, Verbindung

HRID 2228464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2228464
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[I-].[K+].Cl[CH:11]1[C:20]2[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1>CN(C=O)C>[F:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[CH:11]([N:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)[CH2:12][CH2:13][CH2:14]2

Komponenten

5

Edukt 3

HCID 4875Potassium IodideHCID 68163Hexahydro-1,4-diazepineHCID 184699331-Chloro-6-fluoro-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 18469945HCID 18469945, VerbindungAusbeute 17.403,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Under nitrogen atmosphere, a 3-necked 500 ml round-bottomed flask was charged with homopiperazine (20 mg), DMF (130 ml) and potassium iodide (0.35 g). A solution of 7.70 g (41.7 mmol) of 1-chloro-6-fluoro-1,2,3,4-tetrahydronaphthalene in 39 ml of DMF was added over a five minute period. The mixture was stirred at 55°-60° C. for two hours and then at ambient temperature overnight. Tlc analysis on silica gel (diethyl ether:hexane 5:95) showed the absence of the starting halide, Rf 0.77. Most of the DMF was then removed in vacuo (35° C., 0.6 torr) using a rotary evaporator. The residue was treated with 300 ml of water and extracted with ethyl acetate which was then dried (MgSO4). Filtration and removal of solvent in vacuo gave a yellow oil which was kugelrohr distilled to give the title compound, (8.63 g), bp (air bath temperature) 155°-166° C. at 0.26 torr, as a viscous yellow oil. 1H NMR (300 MHz, CDCl3) δ 3.86 (t, 1H, ArCHN), 6.78 (dd, 1H), 6.85 (m, 1H), 7.75 (m, 1H). Anal: Calcd. for C15H21FN2: C, 72.55; H, 8.52; N, 11.28. Found: C, 72.05; H, 8.53; N. 10.95. 1-Chloro-6-fluoro-1,2,3,4-tetrahydronaphthalene was prepared as follows:

Aufarbeitung

  1. customat ambient temperature
  2. customovernight
  3. customMost of the DMF was then removed in vacuo (35° C., 0.6 torr)
  4. customa rotary evaporator
  5. additionThe residue was treated with 300 ml of water
  6. extractionextracted with ethyl acetate which
  7. dry with materialwas then dried (MgSO4)
  8. filtrationFiltration and removal of solvent in vacuo
  9. customgave a yellow oil which
  10. distillationwas kugelrohr distilled

Quellen und Nachweise

ORD-Eintrag
ord-a9c9693511f14064a8140b33a74bedac
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06417183B1

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