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Hydrochloric Acid → 4-(4-Fluorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride

HRID 1955186
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1955186
Br.[F:2][C:3]1[CH:16]=[CH:15][C:6](C(C2CCNCC2)=O)=[CH:5][CH:4]=1.[C:17]([N:20]1[CH2:25][CH2:24][CH:23]([C:26](=O)[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:22][CH2:21]1)(=O)[CH3:18].[OH-:35].[Na+].[ClH:37]>>[ClH:37].[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][CH:23]2[CH2:24][CH2:25][N:20]([CH2:17][CH2:18][O:35][C:6]3[CH:15]=[CH:16][C:3]([F:2])=[CH:4][CH:5]=3)[CH2:21][CH2:22]2)=[CH:28][CH:29]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1172571-Acetyl-4-(4-fluorobenzoyl)piperidineHCID 186215174-(p-Fluorobenzoyl)piperidine hydrobromide

Produkt 1

HCID 232944164-(4-Fluorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochlorideAusbeute 98 %

Versuchsvorschrift

4-(4-Fluorobenzoyl)piperidine hydrobromide. A solution of 1-acetyl-4-(4-fluoro-benzoyl)piperidine (1.20 g, 4.80 mmol) in HCl (6N, 15 mL) was refluxed for 2 h. The cooled solution was made basic (NaOH) and then extracted with benzene (2×40 mL). The collected organic phase was washed with brine (50 mL), dried and was concentrated under reduced pressure. The free amine was dissolved in HBr (saturated solution in MeOH, 10 mL). The precipitated hydrobromide salt was collected, washed with ether (2×4 mL) and dried in vacuo to afford the title compound as a colorless solid (1.54 g, 98%): mp 198° C.; 1H NMR (CD3OD) 1.80-2.00 (m, 2H), 2.05-2.18 (m, 2H), 3.12-3.28 (m, 2H), 3.40-3.50 (m, 2H), 3.70-3.85 (m, 1H), 4.85 (s, 2H), 7.24 (t, J=8.3 Hz, 2H), 8.10 (dd, J=5.7 and 8.7 Hz, 2H).

Aufarbeitung

  1. extractionextracted with benzene (2×40 mL)
  2. washThe collected organic phase was washed with brine (50 mL)
  3. customdried
  4. concentrationwas concentrated under reduced pressure
  5. dissolutionThe free amine was dissolved in HBr (saturated solution in MeOH, 10 mL)
  6. customThe precipitated hydrobromide salt was collected
  7. washwashed with ether (2×4 mL)
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-46268b5e9b1043468e2ab5c29130bcef
Quelldatensatz
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06124323

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