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

HRID 443297Notes

Reaction equation

HRID 443297 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
70 °C

Procedure

A mixture of 1-benzyl-4-cyano-4-(3-methylphenylamino)-piperidine (7.6 g) and 90% sulfuric acid (53 mL) was heated 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.

Workup

  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

Sources & evidence

ORD record
ord-70eed4828b224ba8961b0d870967015b
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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