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Hydrochloric Acid → N-{1-[2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethyl]-4-piperidyl}-4-fluorobenzamide hydrochloride

HRID 1493873
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1493873
Br[CH2:2][CH2:3][CH:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1.[ClH:14].[NH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:30])[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>CC(=O)CC.CC(C)=O.C(O)(C)C>[ClH:14].[O:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:4]([CH2:3][CH2:2][N:15]2[CH2:16][CH2:17][CH:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:19][CH2:20]2)[CH2:5][CH2:6]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 143302824-(2-bromoethyl)-3,4-dihydro-2H-benzopyranHCID 198294144-Fluoro-N-(piperidine-4-yl)benzamide hydrochloride

Produkt 1

HCID 19829444
N-{1-[2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethyl]-4-piperidyl}-4-fluorobenzamide hydrochloride
Ausbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

The procedure is as in Example 4, but starting with 4-(2-bromoethyl)-3,4-dihydro-2H-benzopyran (1.9 g), N-(4-piperidyl)-4-fluorobenzamide hydrochloride (2 g), dry potassium carbonate (2.15 g) and potassium iodide (0.95 g) in 2-butanone (60 cc). The yellow oil obtained is purified by chromatography on a column 4 cm in diameter containing a silica gel (110 g), eluting with a toluene/diethylamine/ethanol mixture (60:20:20 by volume) (300 cc) and collecting 30-cc fractions. The fractions between 330 and 900 cc are concentrated to dryness. The yellow crystals obtained are dissolved in acetone (25 cc) and treated with a 3.4N solution (3 cc) of hydrochloric acid in isopropanol. The precipitate formed is filtered off on sintered glass and then recrystallized in an ethanol/acetone mixture (20:60 by volume) (80 cc). After the addition of ethyl ether (10 cc), N-{1-[2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethyl]-4-piperidyl}-4-fluorobenzamide hydrochloride (2.05 g) is obtained in the form of a crystalline white solid, m.p. 240° C.

Aufarbeitung

  1. customThe yellow oil obtained
  2. customis purified by chromatography on a column 4 cm in diameter
  3. additioncontaining a silica gel (110 g)
  4. washeluting with a toluene/diethylamine/ethanol mixture (60:20:20 by volume) (300 cc)
  5. customcollecting 30-cc fractions
  6. concentrationThe fractions between 330 and 900 cc are concentrated to dryness
  7. customThe yellow crystals obtained
  8. customThe precipitate formed
  9. filtrationis filtered off on sintered glass
  10. customrecrystallized in an ethanol/acetone mixture (20:60 by volume) (80 cc)
  11. additionAfter the addition of ethyl ether (10 cc)

Quellen und Nachweise

ORD-Eintrag
ord-b6992bca6f8247e4894f784274d32a19
Quelldatensatz
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05025013

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