Pyridine → N-(3-chloro-4-methoxyphenylcarbonyl)-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine

HRID 1683839

Reaktionsgleichung

Reaktionsgleichung von HRID 1683839
[F:1][C:2]([F:30])([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)([OH:17])[CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1.N1C=CC=CC=1.[Cl:37][C:38]1[CH:39]=[C:40]([CH:44]=[CH:45][C:46]=1[O:47][CH3:48])[C:41](Cl)=[O:42]>O1CCCC1>[Cl:37][C:38]1[CH:39]=[C:40]([C:41]([N:14]2[CH2:15][CH2:16][CH:11]([C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:29])([F:1])[F:30])=[CH:9][CH:8]=3)([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:26])[F:27])=[CH:20][CH:19]=3)[OH:17])[CH2:12][CH2:13]2)=[O:42])[CH:44]=[CH:45][C:46]=1[O:47][CH3:48]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 47692993-Chloro-4-methoxybenzoyl chlorideHCID 190409264-[Bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine

Produkt 1

HCID 19040922N-(3-chloro-4-methoxyphenylcarbonyl)-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In a separate reaction vessel, a solution of 0.5 gram (0.0012 mole) of 4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine (prepared in Step B of Example 7) and 0.09 gram (0.0012 mole) of pyridine in a small amount of tetrahydrofuran was stirred, and the solution of 3-chloro-4-methoxybenzoyl chloride in tetrahydrofuran, prepared above, was added. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 15 minutes and then filtered to remove a white solid. The filtrate was stirred for about 18 hours and then was partitioned between ethyl acetate and an aqueous solution saturated with sodium chloride. The organic layer was separated and passed through a column of silica gel. Elution was accomplished with 50% ethyl acetate in hexane. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.62 gram of N-(3-chloro-4-methoxyphenylcarbonyl)-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. customIn a separate reaction vessel
  2. additionwas added
  3. additionUpon completion of addition
  4. filtrationfiltered
  5. customto remove a white solid
  6. stirringThe filtrate was stirred for about 18 hours
  7. customwas partitioned between ethyl acetate
  8. customThe organic layer was separated
  9. washElution
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-44dc4ca3cad84db4b0d21a10c2d87875
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639763

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