Sodium Iodide → HCID 58574632, compound

HRID 1619326Notes

Reaction equation

HRID 1619326 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][C:7]1([CH3:12])[CH2:11][CH2:10][CH2:9][NH:8]1)=[O:4].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N.O>[CH3:12][C:7]12[CH2:11][CH2:10][CH2:9][N:8]1[CH2:2][C:3](=[O:4])[NH:5][CH2:6]2

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 58574251HCID 58574251, compound

Product 1

HCID 58574632HCID 58574632, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-chloro-N-((2-methylpyrrolidin-2-yl)methyl)acetamide (˜300 mg), K2CO3 (1.0 g, 7.2 mmol) and a catalytic amount of NaI in CH3CN was stirred at 80° C. for about 3 h. The reaction was monitored by LC-MS. After cooling to room temperature, the suspension was diluted with water (30 mL) and extracted with DCM (8×100 mL). Then the combined organic layers were concentrated to give 120 mg of the desired product, which was directly used for the next step without further purification. MS (ESI): 155 (MH+).

Workup

  1. extractionextracted with DCM (8×100 mL)
  2. concentrationThen the combined organic layers were concentrated

Sources & evidence

ORD record
ord-2c2bd805cf0c42f5b424aa2107297ed5
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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