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Succinimide → N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-4-succinimidomethylbenzamide

HRID 2474
Notes
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Reaction equation

HRID 2474 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])[C:17](=[O:26])[C:18]3[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:37]1(=[O:43])[NH:41][C:40](=[O:42])[CH2:39][CH2:38]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.O>[F:1][C:2]1[CH:36]=[CH:35][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])[C:17](=[O:26])[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:41]4[C:40](=[O:42])[CH2:39][CH2:38][C:37]4=[O:43])=[CH:20][CH:19]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11439SuccinimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19689926N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-hydroxymethyl-N-(2-methoxyphenyl)benzamide

Product 1

HCID 19689846N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-4-succinimidomethylbenzamide
Yield 66.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of argon, N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-hydroxymethyl-N-(2-methoxyphenyl)benzamide (54 mg, 0.11 mmol), succinimide (13 mg, 0.132 mmol) and triphenylphosphine (34.6 mg, 0.132 mmol) were dissolved in THF (1 ml) to which was subsequently added dropwise diethyl azodicarboxylate (21 μl, 0.132 mmol) while cooling in an ice bath. After 30 minutes of stirring at room temperature, the reaction solution was diluted with water (10 ml) and extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a PTLC (chloroform:methanol=20:1) to obtain 42 mg (66.8%) of the title compound in a light yellow amorphous form.

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic layer was washed with water and saturated brine
  4. dry with materialdried on anhydrous sodium carbonate
  5. customThereafter, the solvent was removed by evaporation
  6. customthe resulting residue was purified by a PTLC (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-92d7b0faebcf42cd917c0eec104efa76
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728835

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes