Triethylamine → Benzofuran-2-carboxylic Acid (1-benzo[1,3]dioxol-5-yl-cyclopentylmethyl)-amide

HRID 1818081

Reaktionsgleichung

Reaktionsgleichung von HRID 1818081
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:15][NH2:16])[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1[C:26](Cl)=[O:27].C(N(CC)CC)C>O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:15][NH:16][C:26]([C:18]4[O:17][C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=5[CH:19]=4)=[O:27])[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chlorideHCID 199605881-(1,3-Benzodioxol-5-yl)cyclopentanemethanamine

Produkt 1

HCID 57884168Benzofuran-2-carboxylic Acid (1-benzo[1,3]dioxol-5-yl-cyclopentylmethyl)-amideAusbeute 17,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

C-(1-Benzo[1,3]dioxol-5-yl-cyclopentyl)-methylamine (43.8 mg, 0.200 mmol) and benzofuran-2-carbonyl chloride (36.1 mg, 0.200 mmol) were dissolved in 2 mL of 1,4-dioxane containing triethylamine (83.6 μL, 0.600 mmol). The reaction mixture was stirred for 15 hours, evaporated to dryness, and purified by reverse phase preparative liquid chromatography to yield the pure product (13.0 mg, 0.0358 mmol, 17.8%). ESI-MS m/z calc. 363.2, found 364.2 (M+1)+. Retention time of 4.22 minutes.

Aufarbeitung

  1. customevaporated to dryness
  2. custompurified by reverse phase preparative liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f650159990624356842d84c38db064e1
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598412B2

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