Acetic Acid → 8-Benzyl-1-(3-methyl-phenyl)-1,3,8-triazaspiro[4,5]dec-2-en-4-one

HRID 565599Notes

Reaction equation

HRID 565599 reaction equation
[CH2:1]([N:8]1[CH2:16][CH2:15][C:11]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)([C:12]([NH2:14])=[O:13])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](O)(=O)C.C(OCC)(OCC)OCC.[OH-].[NH4+]>C1(C)C=CC=CC=1.O>[CH2:1]([N:8]1[CH2:16][CH2:15][C:11]2([N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=3)[CH:25]=[N:14][C:12]2=[O:13])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 31214Ethyl orthoformateHCID 211931981-Benzyl-4-(3-methylphenylamino)isonipecotamide

Product 1

HCID 212683698-Benzyl-1-(3-methyl-phenyl)-1,3,8-triazaspiro[4,5]dec-2-en-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 1-benzyl-4-(3-methylphenylamino)-isonipecotamide (4.3 g, 13.5 mmol) and glacial acetic acid (1.0 mL) in toluene (20 mL) heated under reflux, triethyl orthoformate (2.0 g, 13.5 mmol) was added over a period of 3 h using a syringe pump. The resultant mixture was refluxed for 38 h., and treated with a mixture of concentrated ammonium hydroxide (1.3 mL) and water (3.4 mL). The organic extract was isolated, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was subjected to column chromatography on silica gel eluting with 5% methanol in chloroform. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. extractionThe organic extract
  4. customwas isolated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-ecbf13bea8af42729fc7e6a7265f32be
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

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