Sodium Iodide → HCID 53725875, compound

HRID 1769680Notes

Reaction equation

HRID 1769680 reaction equation
Br[CH:2](Cl)[C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].C([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH:32](C(N)=O)[CH2:31]1)=O)(C)(C)C>CN(C)C=O>[CH3:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH3:12])[C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:33]1[CH2:34][CH2:35][N:30]([CH:28]=[O:27])[CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 11042527Tert-butyl 3-carbamoylpiperazine-1-carboxylateHCID 20096923HCID 20096923, compound

Product 1

HCID 53725875HCID 53725875, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-bromo,chloro-N-(2,6-dimethylphenyl)acetamide (V: 24.2 g, 0.10 mol), anhydrous sodium carbonate (15.9 g, 0.15 mol), sodium iodide (0.10 g) and 1-piperazine carboxaldehyde (IV: 10.3 mL, 0.10 mol) in anhydrous dimethylformamide (200 mL) was heated to 85° C. for 6 h before it was cooled, suction-filtered and concentrated down in vacuo. The residue was then dissolved in a minimal amount of hot 5% methanol in ethyl acetate. After 2 h at ambient temperature, the mixture was suction-filtered and the filtrate was concentrated down once again to yield a grey-colored solid which was recrystallized from ethyl acetate. There the Formula III compound was isolated 17.95 g (65%) as a white solid, m.p. 139°-140° C.; 1H NMR (300 MHz, CDCl3) δ 8.50 (br s, 1H), 7.99 (s, 1H), 7.25-7.03 (m, 3H), 3.59-5.56 (m, 2H), 3.42-3.39 (m, 2H), 3.17 (s, 2H), 2.66-2.59 (m, 4H), 2.19 (s, 6H); 13C NMR (75 MHz, CDCl3) ppm 167.96, 160.96, 135.18, 133.67, 128.53, 127.55, 61.89, 54.28, 53.21, 45.69, 40.07, 18.83; IR (KBr) 3432, 3274, 2958, 1672, 1506, 1446, 1436, 1148, 1020, 1008, 788 cm-1 ; MS m/z calc'd for C15H22N3O2 276.1712, found 276.1709.

Workup

  1. temperaturewas cooled
  2. filtrationsuction-filtered
  3. concentrationconcentrated down in vacuo
  4. dissolutionThe residue was then dissolved in a minimal amount of hot 5% methanol in ethyl acetate
  5. filtrationthe mixture was suction-filtered
  6. concentrationthe filtrate was concentrated down once again
  7. customto yield a grey-colored solid which
  8. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-94c93f58021e47d892d0322da5bbcd22
Source dataset
uspto-grants-1995_01
Patent number
US05382584

Reaction notes

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