Acetic Acid → HCID 178418702, Verbindung

HRID 1744348

Reaktionsgleichung

Reaktionsgleichung von HRID 1744348
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.Cl.[OH-:18].[Na+].N1([CH2:26][NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)CCCCC1.[C:34](O)(=O)[CH3:35]>O>[N:9]1([CH2:8][C:7]2[CH:15]=[CH:16][C:4]([NH:1][CH:34]=[C:35]3[C:29]4[C:28](=[CH:33][CH:32]=[CH:31][CH:30]=4)[NH:27][C:26]3=[O:18])=[CH:5][CH:6]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 7835411-(4-Nitrobenzyl)piperidineHCID 21974891Piperidin-1-ylmethyl-phenylamine

Produkt 1

HCID 178418702HCID 178418702, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1-(4-Nitro-benzyl)-piperidine (0.5052 gms.) is suspended in 25 mL of a 1:1 (v:v) solution of acetic acid and water. The suspension is then treated with 45 mL of an ˜10 wt. % solution of TiCl3 in 20–30 wt. % HCl, dropwise. Over the course of the addition a color change from colorless to purple to black ensues. The reaction mixture is immersed in a 60° C. oil bath overnight following the addition of TiCi3. The reaction mixture is then cooled to room temperature and made basic with the addition of a 10% aqueous solution of NaOH. The basic reaction mixture is extracted with chloroform, and the organic layer is dried over anhydrous sodium sulfate. Following evaporation of the solvent the organic layer yields 0.333 gms. of piperidin-1-ylmethyl-phenylamine.

Aufarbeitung

  1. additionOver the course of the addition a color change from colorless to purple to black ensues
  2. customis immersed in a 60° C.
  3. customovernight
  4. additionthe addition of TiCi3
  5. customThe basic reaction mixture
  6. extractionis extracted with chloroform
  7. dry with materialthe organic layer is dried over anhydrous sodium sulfate
  8. customevaporation of the solvent the organic layer
  9. customyields 0.333 gms

Quellen und Nachweise

ORD-Eintrag
ord-5e5c9dce0d7a42d7ad8e81a3d4b8ce23
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015220B2

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