Sodium Iodide → HCID 57917668, compound

HRID 1878382Notes

Reaction equation

HRID 1878382 reaction equation
[CH3:1][C@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C:15]([NH:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27]Cl)[CH:22]=1)([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[C:15]([NH:19][C:20]([C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=1)[CH2:27][N:7]1[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][C@H:2]1[CH3:1])=[O:29])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2756811(R)-1-Boc-3-methylpiperazineHCID 43156221N-tert-butyl-3-(chloromethyl)benzamide

Product 1

HCID 57917668HCID 57917668, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-tert-Butyl 3-methylpiperazine-1-carboxylate was added to a solution containing N-tert-butyl-3-(chloromethyl)benzamide (3.38 g, 14.9 mmol), potassium carbonate (4.11 g, 29.8 mmol) and sodium iodide (catalytic amount) in acetonitrile. The reaction was stirred under reflux for 2 hours. The acetonitrile was removed under reduced pressure. The resulting residue was taken up in dichloromethane and filtered. The filtrate was concentrated under vacuum to afford the title compound (5.82 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe acetonitrile was removed under reduced pressure
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-b60f1d79c1b74f509609ff5de287a99f
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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