Sulfuric Acid → 1-Benzyl-4-(3-methylphenylamino)isonipecotamide

HRID 565598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 565598
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:22]#[N:23])([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:25].[OH-].[NH4+]>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)([C:22]([NH2:23])=[O:25])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 14923Ammonium Hydroxide2×HCID 704161-Benzyl-4-(m-toluidino)piperidine-4-carbonitrile

Produkt 1

HCID 211931981-Benzyl-4-(3-methylphenylamino)isonipecotamide

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1-benzyl-4-cyano-4-(3-methylphenylamino)-piperidine (7.6 g) and 90% sulfuric acid (53 mL) was heated at 70° C. until all the solid dissolved (˜1 h). The resultant mixture was stirred at the temp. for 30 min., and poured into a mixture of ice (80 g) and concentrated ammonium hydroxide (75 g). The solution was basified with ammonium hydroxide, and extracted with chloroform. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title compound.

Aufarbeitung

  1. dissolutiondissolved (˜1 h)
  2. extractionextracted with chloroform
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1949cc2091a14827ba4818e35871641d
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172076B2

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