Potassium Iodide → Fluperamide hydrochloride

HRID 482376

Reaktionsgleichung

Reaktionsgleichung von HRID 482376
[Br-].[CH3:2][N+:3]([CH3:21])=[C:4]1[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][O:5]1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2([OH:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][C:24]=1[C:36]([F:39])([F:38])[F:37].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[ClH:22].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2([OH:35])[CH2:30][CH2:31][N:32]([CH2:6][CH2:7][C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]([N:3]([CH3:21])[CH3:2])=[O:5])[CH2:33][CH2:34]2)=[CH:25][C:24]=1[C:36]([F:39])([F:37])[F:38]

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 891074-(4-Chloro-3-(trifluoromethyl)phenyl)piperidin-4-olHCID 2723589(Dihydro-3,3-diphenyl-3H-furan-2-ylidene)dimethylammonium bromide

Produkt 1

HCID 214899Fluperamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 12.1 parts of dimethyl (tetrahydro-3,3-diphenyl-2-furylidene) ammonium bromide, 8.4 parts of 4-(4-chloro-3-trifluoromethylphenyl)-4-piperidinol, 8 parts of sodium carbonate, 0.4 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 3 hours with water separator. The reaction mixture is cooled and water is added. The organic layer is separated, washed with diluted sodium hydroxide solution, dried and concentrated to a volume of about 200 parts. The concentrate is acidified with an excess of 2-propanol previously saturated with gaseous hydrogen chloride. Upon stirring, the salt is crystallized. It is filtered off and dried, yielding 4-(4-chloro-3-trifluoromethylphenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenylpiperidine-1 -butyramide hydrochloride; m.p. 215.3° C.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. customThe organic layer is separated
  3. washwashed with diluted sodium hydroxide solution
  4. customdried
  5. concentrationconcentrated to a volume of about 200 parts
  6. stirringUpon stirring
  7. customthe salt is crystallized
  8. filtrationIt is filtered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-effb472a09b042e7b8ac8bd1b6b0e56d
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05798093

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