Triethylamine → HCID 1120195, Verbindung

HRID 1818074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818074
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:16][NH2:17])[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[O:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH:27]=[C:26]1[C:34](Cl)=[O:35]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:16][NH:17][C:34]([C:26]3[O:25][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[CH:27]=3)=[O:35])[CH2:12][CH2:13][CH2:14][CH2:15]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chlorideHCID 739193STK362959

Produkt 1

HCID 1120195HCID 1120195, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

C-[1-(3,4-Dimethoxy-phenyl)-cyclopentyl]-methylamine (141 mg, 0.600 mmol) was dissolved in anhydrous 1,4-dioxane (2 mL) containing triethylamine (167 μL, 1.20 mmol). Benzofuran -2-carbonyl chloride (108 mg, 0.600 mmol) was then added and the reaction mixture was allowed to stir for 16 hours. The reaction mixture was filtered, evaporated to dryness, and purified by column chromatography on silica gel using a gradient of 5-50% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a white solid (0.1775 g, 0.4678 mmol, 78.0%) ESI-MS m/z calc. 379.5, found 380.2 (M+1)+. Retention time of 3.36 minutes. 1H NMR (400 MHz, DMSO-d6) δ 1.57-2.03 (m, 8H), 3.46 (d, J=6.4 Hz, 2H), 3.72 (s, 6H), 6.81-6.89 (m, 3H), 7.31 (t, J=7.5 Hz, 1H), 7.44 (t, J=7.8 Hz, 1H), 7.48 (s, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.75 (d, J=8.4 Hz, 1H), 7.94 (t, J=6.3 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ 23.1, 35.3, 47.2, 51.8, 55.5, 109.2, 111.5, 111.6, 111.7, 118.8, 122.6, 123.6, 126.7, 127.1, 139.3, 147.1, 148.3, 149.1, 154.1, 158.2.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. custompurified by column chromatography on silica gel using a gradient of 5-50% ethyl acetate in hexanes
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1059de7be54140e3a6d2c7cb49b67dc2
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598412B2

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