4-Fluorobenzoyl chloride → Ethyl 1-(4-fluorobenzoyl)piperidine-3-carboxylate

HRID 432793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432793
[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCCC(C(OCC)=O)C1.[F:31]C1C=CC(C(Cl)=O)=CC=1>>[F:31][C:5]1[CH:4]=[CH:3][C:2]([C:1]([N:9]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]2)=[O:8])=[CH:7][CH:6]=1

Komponenten

4

Edukt 3

HCID 678794-Fluorobenzoyl chlorideHCID 98969Ethyl nipecotateHCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylate

Produkt 1

HCID 2905457Ethyl 1-(4-fluorobenzoyl)piperidine-3-carboxylate

Versuchsvorschrift

The reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with ethyl nipecotate (230.9 mg; 1.47 mmol) and commercially available 4-fluorobenzoyl chloride (173 μl; 1.47 mmol). The crude product was distilled at 220° C./0.1 torr, giving ethyl 1-(4-fluorobenzoyl)-3-piperidinecarboxylate (283.4 mg) as a light yellow oil. MS m/z (positive ion) 581 (dimer+Na+; 50), 302 (M+Na+; 100), 280 (MH+; 95), 234 (45), 229 (25), 158 (50), 122.5 (60).

Aufarbeitung

  1. distillationThe crude product was distilled at 220° C./0.1 torr

Quellen und Nachweise

ORD-Eintrag
ord-ac962e93c52747d4950d4c6c9ecd1462
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664271B1

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