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

HRID 1068487Notes

Reaction equation

HRID 1068487 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-882d7f20507c4e8b8944a74d10b878b2
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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