Sodium Iodide → HCID 57917626, compound

HRID 1878423Notes

Reaction equation

HRID 1878423 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:15][C:16]1[CH:17]=[C:18]([CH:26]=[CH:27][CH:28]=1)[C:19]([NH:21][CH:22]1[CH2:25][CH2:24][CH2:23]1)=[O:20].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.C(OCC)(=O)C.O>[CH:22]1([NH:21][C:19]([C:18]2[CH:17]=[C:16]([CH:28]=[CH:27][CH:26]=2)[CH2:15][N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[O:20])[CH2:25][CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 62414168HCID 62414168, compound

Product 1

HCID 57917626HCID 57917626, compoundYield 98.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of tert-butyl piperazine-1-carboxylate (8.94 mmol, 1.665 g), 3-(chloromethyl)-N-cyclobutylbenzamide (8.94 mmol, 2 g), potassium carbonate (17.88 mmol, 2.471 g) and sodium iodide (0.894 mmol, 0.134 g) in acetonitrile (50 ml) was heated at 80° C. for 3 hours. The reaction mixture was diluted with ethyl acetate and water. The organic layer was separated, dried (magnesium sulfate) and concentrated under reduced pressure to give the title compound (3.3 g). MS (ESI) m/z 374.4 ([M+H]+).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f73795f1e5e4f6cb6f4a38902a5d24e
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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