N-Hydroxyphthalimide → HCID 21535544, compound

HRID 1076967Notes

Reaction equation

HRID 1076967 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])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]2[C:35]1=[O:44].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:35](=[O:44])[C:36]3=[CH:43][CH:42]=[CH:41][CH:40]=[C:37]3[C:38]2=[O:39])=[O:13])[CH2:8][CH2:7]1)#[N:2]

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 10868DicyclohexylcarbodiimideHCID 34328Difenoxin

Product 1

HCID 21535544HCID 21535544, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.12 Grams of 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid are dissolved in 65 ml. of redistilled N,N-dimethylformamide by warming to about 60°C. To the warm solution is added, with stirring, .82 gram of N-hydroxyphthalimide, followed by 1.16 grams of dicyclohexylcarbodiimide. The resultant mixture is stirred at room temperature under calcium chloride, then cooled and filtered. The filtrate is diluted with water and extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried over potassium carbonate and partially concentrated until a precipitate forms. Filtration and repeated crystallizations of the precipitate from a mixture of chloroform and hexane affords N-[1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carbonyloxy]phthalimide, melting at about 156.5°-157.5°C. The product has the formula ##SPC4##

Workup

  1. additionTo the warm solution is added
  2. temperaturecooled
  3. filtrationfiltered
  4. additionThe filtrate is diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer is washed with water
  7. dry with materialdried over potassium carbonate
  8. concentrationpartially concentrated until a precipitate forms
  9. filtrationFiltration
  10. customcrystallizations of the precipitate
  11. additionfrom a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-a81f3c8de6b249958b1210198ef785f2
Source dataset
uspto-grants-1976_05
Patent number
US03959275

Reaction notes

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