Potassium Iodide → HCID 22397675, compound

HRID 1070758Notes

Reaction equation

HRID 1070758 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6].[N-:26]=[N+]=[N-].[Na+].[I-].[K+]>CN(C=O)C>[NH2:26][CH2:2][CH2:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 33557Sodium AzideHCID 4163052HCID 4163052, compound

Product 1

HCID 22397675HCID 22397675, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.9 g (24.9 mmol) 1-(4-chlorobutyryl)-4-diphenylmethylpiperazine, 4.8 g (73.8 mmol) sodium azide, 1 g potassium iodide and 1 g molecular sieve 4A are stirred in 70 ml DMF for five hours at 70° C. After cooling, the reaction mixture is filtered and the filtrate is concentrated under vacuum. The accumulated crude product is dissolved in methanol and mixed with a spatula tip of palladium-carbon (10%). The mixture is stirred for two days at RT under hydrogen atmosphere. The mixture is filtered from the catalyst and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH/TEA (90/10/5): yield 5.2 g (62%) as a colorless amorphous solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under vacuum
  4. dissolutionis dissolved in methanol
  5. additionmixed with a spatula tip of palladium-carbon (10%)
  6. filtrationThe mixture is filtered from the catalyst
  7. customthe solvent is removed under vacuum
  8. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH/TEA (90/10/5)

Sources & evidence

ORD record
ord-85ddde3998ff485f99565a31130e67ae
Source dataset
uspto-grants-2005_06
Patent number
US06903118B1

Reaction notes

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