N-Hydroxyphthalimide → HCID 21535544, compound

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

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##