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

HRID 1638217Notes

Reaction equation

HRID 1638217 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2([C:22]([NH2:24])=[O:23])[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[CH:25](OCC)(OCC)OCC>>[CH2:15]([N:12]1[CH2:11][CH2:10][C:9]2([N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[CH:25]=[N:24][C:22]2=[O:23])[CH2:14][CH2:13]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 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

Conditions

Temperature
150 °C

Procedure

4-(3-methyl-phenyl-amino)-1-(phenylmethyl)-4-piperidine-carboxamide (12.94 g) was dissolved in 80 ml triethyl orthoformate and stirred at 150° C. for 66 hours. After cooling to 0° C., the reaction mixture was filtered and the light brown powder washed with ether to yield 8-benzyl-1-(3-methyl-phenyl)-1,3,8-triazaspiro[4,5]dec-2-en-4-one (2.1g). M.p. 301.5-302.6° C.

Workup

  1. temperatureAfter cooling to 0° C.
  2. filtrationthe reaction mixture was filtered
  3. washthe light brown powder washed with ether

Sources & evidence

ORD record
ord-d1b028fd2db2434c8de30b87c84c19eb
Source dataset
uspto-grants-2000_03
Patent number
US06043366

Reaction notes

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