4-Fluoroaniline → Diisopropyl Ether

HRID 49793

Reaktionsgleichung

Reaktionsgleichung von HRID 49793
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH:13]N1[C:18]2C=CC=[CH:22][C:17]=2N=N1.Cl.[CH2:24](N=C=NCCC[N:32]([CH3:34])C)C.[F:35][C:36]1[CH:42]=[CH:41][C:39](N)=[CH:38][CH:37]=1>ClCCl>[CH:17]([O:12][CH:10]([CH3:7])[CH3:24])([CH3:22])[CH3:18].[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:39]2[CH:41]=[CH:42][C:36]([F:35])=[CH:37][CH:38]=2)[CH2:8][CH:9]1[C:34](=[O:13])[NH2:32])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 97314-FluoroanilineHCID 757711-HydroxybenzotriazoleHCID 1172551-Acetylpiperidine-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 2

HCID 7914Diisopropyl EtherHCID 227418291-Acetyl-4-(4-fluorophenyl)-carbamoylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of N-acetylpiperidine-4-carboxylic acid (514 mg), 1-hydroxybenzotriazole (405 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (575 mg) and 4-fluoroaniline (284.2 ml) in dichloromethane (5 ml) was stirred for 18 hours at ambient temperature. The mixture was diluted with dichloromethane and washed with water, saturated aqueous sodium hydrogen carbonate, water, and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. A residue was purified by column chromatography (silica gel 40 ml, dichloromethane:methanol=15:1). After trituration with diisopropyl ether, 1-acetyl-4-(4-fluorophenyl)-carbamoylpiperidine (532 mg) was obtained.

Aufarbeitung

  1. washwashed with water, saturated aqueous sodium hydrogen carbonate, water, and brine
  2. dry with materialAfter drying with magnesium sulfate
  3. customthe solvents were removed under reduced pressure
  4. customA residue was purified by column chromatography (silica gel 40 ml, dichloromethane:methanol=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-7d7f0fcf5281400cbfb6b320c8612b93
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710043B1

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