Sodium Iodide → HCID 66878540, compound

HRID 1878428Notes

Reaction equation

HRID 1878428 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.[C@H:14]([NH:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26]Cl)[CH:21]=1)([CH2:16][CH3:17])[CH3:15].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.C(OCC)(=O)C.O>[C@H:14]([NH:18][C:19]([C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[CH2:26][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)=[O:28])([CH2:16][CH3:17])[CH3:15]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 66878657HCID 66878657, compound

Product 1

HCID 66878540HCID 66878540, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of tert-butyl piperazine-1-carboxylate (5.32 mmol, 0.990 g), (R)—N-sec-butyl-3-(chloromethyl)benzamide (5.32 mmol, 1.2 g), potassium carbonate (10.63 mmol, 1.469 g) and sodium iodide (0.532 mmol, 0.080 g) in acetonitrile (50 mL) were 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 (2 g). MS (ESI) m/z 376.5 [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-93397fafad53434b85cb177b9145dc77
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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