Triethylamine → Cyclopropanecarboxylic acid [3-(7-fluoro-2,3-dihydro-benzofuran-4-yl)propyl]amide

HRID 1602419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1602419
[F:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[C:5]([CH2:11][CH2:12][CH2:13][NH2:14])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>ClCCl>[F:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[C:5]([CH2:11][CH2:12][CH2:13][NH:14][C:25]([CH:22]2[CH2:24][CH2:23]2)=[O:26])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 196116493-(7-Fluoro-2,3-dihydro-benzofuran-4-yl)-propylamine

Produkt 1

HCID 54235850Cyclopropanecarboxylic acid [3-(7-fluoro-2,3-dihydro-benzofuran-4-yl)propyl]amideAusbeute 10,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-(7-fluoro-2,3-dihydro-benzofuran-4-yl)-propylamine (114 mg), triethylamine (0.089 ml), dichloromethane (5 ml) and cyclopropanecarbonyl chloride (67 mg) was stirred in ice for 20 minutes and stirring continued at room temperature overnight. The mixture was partitioned between 2N hydrochloric acid and dichloromethane and the organic phase washed with 8% sodium bicarbonate and evaporated. Purification of the residue by preparative hplc gave the title compound as a white solid (16 mg).

Aufarbeitung

  1. stirringstirring
  2. waitcontinued at room temperature overnight
  3. customThe mixture was partitioned between 2N hydrochloric acid and dichloromethane
  4. washthe organic phase washed with 8% sodium bicarbonate
  5. customevaporated
  6. customPurification of the residue by preparative hplc

Quellen und Nachweise

ORD-Eintrag
ord-cf80e80104c3420bb674f3d80f12c322
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05981572

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