Acetic Anhydride → N-{1-[1-(4-Chloro-benzoyl)-4-hydroxy-pyrrolidin-3-yl]-piperidin-4-yl}-N-(4-chloro-phenyl)-acetamide

HRID 1947090Notes

Reaction equation

HRID 1947090 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH:13]([OH:15])[CH:12]([N:16]3[CH2:21][CH2:20][CH:19]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)[CH2:18][CH2:17]3)[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH3:30][C:31](OC(C)=O)=[O:32]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]2[CH2:14][CH:13]([OH:15])[CH:12]([N:16]3[CH2:17][CH2:18][CH:19]([N:22]([C:23]4[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=4)[C:31](=[O:32])[CH3:30])[CH2:20][CH2:21]3)[CH2:11]2)=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 68512735HCID 68512735, compound

Product 1

HCID 68511424N-{1-[1-(4-Chloro-benzoyl)-4-hydroxy-pyrrolidin-3-yl]-piperidin-4-yl}-N-(4-chloro-phenyl)-acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The starting materials (4-Chloro-phenyl)-{3-[4-(4-chloro-phenylamino)-piperidin-1-yl]-4-hydroxy-pyrrolidin-1-yl}-methanone (48 mg, 0.11 mmol) and Ac2O (16 uL, 0.17 mmol) were added in pyridine (0.5 mL) and stirred at room temperature overnight. The reaction mixture was concentrated down to dryness. The resulting crude residue was purified by column chromatography on silica (Methanol\CH2Cl2: 0%-6%).

Workup

  1. concentrationThe reaction mixture was concentrated down to dryness
  2. customThe resulting crude residue was purified by column chromatography on silica (Methanol\CH2Cl2: 0%-6%)

Sources & evidence

ORD record
ord-1e0ea49ce912489cb1e77d99328fd32a
Source dataset
uspto-grants-2013_03
Patent number
US08399455B2

Reaction notes

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