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Methyl iodide → HCID 68511681, compound

HRID 1947089
Notes
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Reaction equation

HRID 1947089 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]3[CH:18]([OH:19])[CH2:17][N:16]([C:20]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)=[O:21])[CH2:15]3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:33]I>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH:14]3[CH:18]([O:19][CH3:33])[CH2:17][N:16]([C:20]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)=[O:21])[CH2:15]3)[CH2:12][CH2:13]2)=[O:7])=[CH:29][CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68513610HCID 68513610, compound

Product 1

HCID 68511681HCID 68511681, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
4 °C

Procedure

To a cold (3-5° C.) solution of starting material {3-[4-(4-Chloro-benzoyl)-piperazin-1-yl]-4-hydroxy-pyrrolidin-1-yl}-(4-chloro-phenyl)-methanone in 1 mL of NMP was added NaH (4 mg, 0.17 mmol). The mixture was then stirred at 3-5° C. for 15 mins. MeI (7.5 uL) was then added. After 2 hours, the reaction was quenched by adding 50 μL AcOH. The mixture was then partitioned in EtOAc and 1M K2CO3. The separated organic phase was washed with brine, dried over Na2SO4 and concentrated down to dryness. The resulting crude residue was purified by column chromatography on silica (Methanol 1 CH2Cl2: 0%-10%). The pure product was converted to it HCl salt by precipitation in a mixture of ethanol\ether and conc. HCl, to give 43 mg of salt of {3-[4-(4-Chloro-benzoyl)-piperazin-1-yl]-4-methoxy-pyrrolidin-1-yl}-(4-chloro-phenyl)-methanone as a white solid.

Workup

  1. waitAfter 2 hours
  2. customthe reaction was quenched
  3. additionby adding 50 μL AcOH
  4. customThe mixture was then partitioned in EtOAc
  5. washThe separated organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated down to dryness
  8. customThe resulting crude residue was purified by column chromatography on silica (Methanol 1 CH2Cl2: 0%-10%)
  9. customThe pure product was converted to it HCl salt by precipitation in a mixture of ethanol\ether and conc. HCl

Sources & evidence

ORD record
ord-bb6208b9b33e4df686e8501fddc16989
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399455B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes