Sodium Iodide → Tert-butyl 4-(2-iodoacetyl)piperazine-1-carboxylate

HRID 923649Notes

Reaction equation

HRID 923649 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].[I-:18].[Na+]>CC(C)=O>[I:18][CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 15829156Tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate

Product 1

HCID 67174982Tert-butyl 4-(2-iodoacetyl)piperazine-1-carboxylateYield 84.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate (150 mg, 0.57 mmol) and sodium iodide (260 mg, 1.73 mmol) in acetone (6 mL) was stirred at room temperature for 21 h, and then the reaction mixture turned to a suspension containing white solid. The solids were eliminated by filtration, and the filtrate was dried to vacuo and washed with CH2Cl2 and H2O. The organic layer then dried over MgSO4, filtered and concentrated to give tert-butyl 4-(2-iodoacetyl)piperazine-1-carboxylate (164.4 mg, 84.4% yield). C11H191N2O3; brown solid; mp 69-71° C.; IR vmax (neat) 2976, 2926, 2861, 1696, 1650, 1459, 1419, 1366, 1258, 1168, 1028, 996, 750 cm−1; 1H NMR (400 MHz, CDCl3) δ 3.76 (2H, s), 3.57 (2H, m), 3.51 (2H, m), 3.41 (4H, m) 1.47 (9H, s); 13C NMR (100 MHz, CDCl3) δ 166.5, 154.2, 80.4, 47.0, 43.0 (2×), 41.9 (2×), 28.4 (3×).

Workup

  1. additioncontaining white solid
  2. filtrationThe solids were eliminated by filtration
  3. customthe filtrate was dried to vacuo
  4. washwashed with CH2Cl2 and H2O
  5. dry with materialThe organic layer then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3c643218a7aa465dadbaaab37bb43b65
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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