1-Chloroethyl chloroformate → HCID 58772391, Verbindung

HRID 1361514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361514
C([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])([F:14])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClCCl>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]([O:22][CH3:23])=[C:15]([C:11]2([F:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:20]=1

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 58772512HCID 58772512, Verbindung

Produkt 1

HCID 58772391HCID 58772391, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-benzyl-4-(5-chloro-2-methoxy-phenyl)-4-fluoro-piperidine 4c (13.8 g, 0.04 mol) in dichloromethane (50 mL) was added 1-chloroethylchloroformate. (7.1 g, 0.05 mol). The mixture was stirred at room temperature for 2 h and then concentrated to dryness. The residual was dissolved in methanol (50 mL) and then heated to reflux for 30 min. The mixture was concentrated to dryness in vacuo, ether was added, the precipitate solid was filtered and washed with ether to obtain 4-(5-chloro-2-methoxyphenyl)-4-fluoropiperidine 4d as its hydrochloride salt. 1H NMR (DMSO-d6): δ 9.10-9.01 (m, 2H), 7.25 (q, J1=8.4 Hz, J2=8.8 Hz, 1H), 7.33 (d, J=2.8 Hz, 1H), 7.12 (d, J=8.8 Hz, 1H), 3.82 (s, 3H), 3.27 (s, 2H), 3.13-3.04 (m, 2H), 2.79-2.66 (m, 2H), 1.924-1.864 (t. 2H). MS (ESI) m/z (M+H+) 243.98.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. dissolutionThe residual was dissolved in methanol (50 mL)
  3. temperatureheated
  4. temperatureto reflux for 30 min
  5. concentrationThe mixture was concentrated to dryness in vacuo, ether
  6. additionwas added
  7. filtrationthe precipitate solid was filtered
  8. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-f4a90dc2068b499e840f48bb32a729c7
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880007B2

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