Sodium Iodide → HCID 57917660, compound

HRID 1878433Notes

Reaction equation

HRID 1878433 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[C:6]([NH:8][CH:9]1[CH2:12][C:11]([F:14])([F:13])[CH2:10]1)=[O:7].[N:18]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[F:13][C:11]1([F:14])[CH2:12][CH:9]([NH:8][C:6]([C:5]2[CH:4]=[C:3]([CH:17]=[CH:16][CH:15]=2)[CH2:2][N:21]2[CH2:20][CH2:19][N:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22]2)=[O:7])[CH2:10]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 668783523-(chloromethyl)-N-(3,3-difluorocyclobutyl)benzamide

Product 1

HCID 57917660HCID 57917660, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(Chloromethyl)-N-(3,3-difluorocyclobutyl)benzamide (12.82 mmol, 3.33 g), tert-butyl piperazine-1-carboxylate (12.82 mmol, 2.388 g), potassium carbonate (38.5 mmol, 5.32 g) and sodium iodide (2.56 mmol, 0.384 g) were combined and heated at reflux in acetonitrile (50 ml) for 2 hours. The solvent was removed under reduced pressure and the residue taken up in dichloromethane, washed with water, dried over sodium sulfate and concentrated under vacuum to afford the title compound (5.179 g).

Workup

  1. temperatureheated
  2. customThe solvent was removed under reduced pressure
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-97e3627ab6f8437cb5236f74099bc6a5
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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