2-Furancarbonyl chloride → Furan-2-carboxylic acid N-(1-Boc-piperidin-3-ylmethyl)-N-phenyl amide

HRID 479792

Reaktionsgleichung

Reaktionsgleichung von HRID 479792
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](Cl)=[O:28]>C(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:27]([C:23]2[O:22][CH:26]=[CH:25][CH:24]=2)=[O:28])[CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Komponenten

4

Edukt 2

HCID 682422-Furancarbonyl chlorideHCID 12972131N-(1-Boc-piperidin-3-ylmethyl)aniline

Produkt 1

HCID 53971984Furan-2-carboxylic acid N-(1-Boc-piperidin-3-ylmethyl)-N-phenyl amideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of N-(1-Boc-piperidin-3-ylmethyl)-aniline 4 (61.0 mg, 0.21 mmol) and piperidinomethyl polystyrene resin (60 mg) in 0.6 mL of dry CH2Cl2 was added 2-furoyl chloride (95%, 35.1 mg, 1.2 eq.) at room temperature. After being shaken at room temperature for 4 hours, the reaction mixture was passed through an aminopropyl NH2 cartridge and washed with CH2Cl2. Removal of CH2Cl2 afforded furan-2-carboxylic acid N-(1-Boc-piperidin-3-ylmethyl)-N-phenyl amide 13 (75 mg, 93%). LRMS 285 (M-100)+.

Aufarbeitung

  1. washwashed with CH2Cl2
  2. customRemoval of CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-d7366c72ee1d411e8fa52d7305432350
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645980B1

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