Diethyl Ether → 1-(Cyclopropylmethyl)-4-(2'-(4"-fluorophenyl)-2'-phenyl-2'-hydroxyethyl)piperidine

HRID 5139

Reaktionsgleichung

Reaktionsgleichung von HRID 5139
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][CH:8]([CH2:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[O:13])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOCC.[NH4+].[Cl-]>O1CCCC1>[CH:1]1([CH2:4][N:5]2[CH2:6][CH2:7][CH:8]([CH2:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[OH:13])[CH2:9][CH2:10]2)[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 121968DUP-734 free baseHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 190921681-(Cyclopropylmethyl)-4-(2'-(4"-fluorophenyl)-2'-phenyl-2'-hydroxyethyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-(Cyclopropylmethyl)-4-(2'-(4"-fluorophenyl)-2'-oxoethyl)piperidine (Example 429, 1.0 g, 3.6 mmol) was mixed with dry tetrahydrofuran (10 mL). A solution of phenyl magnesium bromide in ether (3.0M, 3 mL, 9 mmol) was added with stirring. The reaction mixture was stirred for 24 h; poured onto a saturated NH4Cl solution and extracted with ethyl acetate three times. The combined organic layers were dried over magnesium sulfate and filtered. Solvent was removed in vacuo. Trituration with ether-hexanes (1:9) and filtration afforded the title compound, a solid, which was dried in vacuo (0.9 g) mp 115°-116° C.; Anal.: Calcd for C23H28FNO: C, 77.36, H, 7.90, N, 3.92, F, 5.32; Found: C, 77.47, 77.41, H, 8.00, 7.92, N, 3.42, 3.52, F, 5.09.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 24 h
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customSolvent was removed in vacuo
  6. filtrationTrituration with ether-hexanes (1:9) and filtration

Quellen und Nachweise

ORD-Eintrag
ord-4a3dc28a00854038bc8f00c5c9d2d330
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05243048

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