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Potassium Iodide → alpha-(4-Methylphenyl)-1-(phenylmethyl)-4-piperidineacetonitrile monohydrochloride

HRID 66671
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 66671
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:9]#[N:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[Cl:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O.CC(C)CC(=O)C>[ClH:25].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:11]2[CH2:12][CH2:13][N:14]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:15][CH2:16]2)[C:9]#[N:10])=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 20530716alpha-(4-Methylphenyl)-4-piperidineacetonitrile

Produkt 1

HCID 13035938alpha-(4-Methylphenyl)-1-(phenylmethyl)-4-piperidineacetonitrile monohydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

To a mixture of 74 parts of dl-α-(4-methylphenyl)-4-piperidineacetonitrile, 95.4 parts of sodium carbonate, a few crystals of potassium iodide in 1840 parts of 4-methyl-2-pentanone are added portionwise 39.21 parts of (chloromethyl)benzene. After the addition is complete, the whole is stirred and refluxed for 24 hours. The reaction mixture is cooled and 400 parts of water are added. The organic layer is separated, dried over potassium carbonate, filtered and evaporated. The oily residue is dissolved in 1,1'-oxybisethane and gazeous hydrogen chloride is introduced into the solution. The precipitated hydrochloride salt is filtered off and dried, yielding 68 parts of dl-α-(4-methylphenyl)-1-(phenylmethyl)-4-piperidineacetonitrile monohydrochloride; mp. 212°-213° C.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturerefluxed for 24 hours
  3. temperatureThe reaction mixture is cooled
  4. customThe organic layer is separated
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe oily residue is dissolved in 1,1'-oxybisethane
  9. additiongazeous hydrogen chloride is introduced into the solution
  10. filtrationThe precipitated hydrochloride salt is filtered off
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9704f32e50604b2286dd4b5de00f0a6f
Quelldatensatz
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04342870

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