Dicyclohexylcarbodiimide → Difenoximide

HRID 1076966Notes

Reaction equation

HRID 1076966 reaction equation
[C:1]([C:3]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)#[N:2].O[N:34]1[C:38](=[O:39])[CH2:37][CH2:36][C:35]1=[O:40].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[C:1]([C:3]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:12]([O:14][N:34]2[C:38](=[O:39])[CH2:37][CH2:36][C:35]2=[O:40])=[O:13])[CH2:8][CH2:7]1)#[N:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 34328DifenoxinHCID 80170N-Hydroxysuccinimide

Product 1

HCID 39481Difenoximide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24.5 Grams of 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid are dissolved in 225 ml. of redistilled N,N-dimethylformamide by warming to about 60°C. To the warm solution were added, with stirring, 9.0 grams of recrystallized N-hydroxysuccinimide, followed by 12.4 grams of dicyclohexylcarbodiimide. A precipitate appears upon cooling to room temperature. The suspension is stirred at room temperature under anhydrous conditions for about 36 hours, then is cooled to approximately 5°C. and is filtered to remove the precipitate. The filtrate is diluted with approximately 400 ml. of ethyl acetate and 200 ml. of water. The organic layer is then separated and washed three times with water, solid sodium chloride being added as needed to break the emulsion formed. The solution is dried over anhydrous sodium sulfate and partially concentrated until a precipitate forms. Filtration and recrystallization of the precipitate from a mixture of tetrahydrofuran and isopropyl ether affords N-[1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carbonyloxy]succinimide, melting at about 156.5°-157.5°C. This product has the formula ##SPC3##

Workup

  1. additionTo the warm solution were added
  2. stirringThe suspension is stirred at room temperature under anhydrous conditions for about 36 hours
  3. temperatureis cooled to approximately 5°C.
  4. filtrationis filtered
  5. customto remove the precipitate
  6. additionThe filtrate is diluted with approximately 400 ml
  7. customThe organic layer is then separated
  8. washwashed three times with water, solid sodium chloride being
  9. additionadded
  10. customformed
  11. dry with materialThe solution is dried over anhydrous sodium sulfate
  12. concentrationpartially concentrated until a precipitate forms
  13. filtrationFiltration and recrystallization of the precipitate
  14. additionfrom a mixture of tetrahydrofuran and isopropyl ether

Sources & evidence

ORD record
ord-ceb85cc66e3345b0ad0eb6a167ed18d2
Source dataset
uspto-grants-1976_05
Patent number
US03959275

Reaction notes

Loading…