Sodium Iodide → HCID 16662377, compound

HRID 548641Notes

Reaction equation

HRID 548641 reaction equation
Cl[CH2:2][CH:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH:19]3[CH3:23])=[CH:10][CH:9]=2)[C:5](=[O:24])[CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH:31]1([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:35][CH2:34][CH2:33][CH2:32]1.[I-].[Na+]>C(#N)C>[CH:31]1([N:36]2[CH2:37][CH2:38][N:39]([CH2:2][CH:3]3[CH2:7][N:6]([C:8]4[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][N:18]5[CH2:22][CH2:21][CH2:20][CH:19]5[CH3:23])=[CH:10][CH:9]=4)[C:5](=[O:24])[CH2:4]3)[CH2:40][CH2:41]2)[CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 8064211-CyclopentylpiperazineHCID 57550245HCID 57550245, compound

Product 1

HCID 16662377HCID 16662377, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(chloromethyl)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one a56 (0.26 g, 0.74 mmol, 1 eq), potassium carbonate (0.4 g, 2.96 mmol, 4 eq), 1-cyclopentylpiperazine a58 (0.34 g, 2.22 mmol, 3 eq) and a catalytic amount of sodium iodide in acetonitrile (20 ml) is stirred at reflux for 4 days. Potassium carbonate is filtered and the mixture is concentrated under vacuum, then the residue is dissolved in ethyl acetate, and washed twice with a saturated solution of aqueous sodium hydrogenocarbonate. The organic layer is dried over magnesium sulfate and concentrated under vacuum to give 0.17 g of crude material. This product is purified by chromatography over silicagel (dichloromethane/methanol/ammonia 94/6/0.6) to afford 0.052 g of 4-[(4-cyclopentylpiperazin-1-yl)methyl]-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one 44 as an orange oil.

Workup

  1. temperatureat reflux for 4 days
  2. filtrationPotassium carbonate is filtered
  3. concentrationthe mixture is concentrated under vacuum
  4. dissolutionthe residue is dissolved in ethyl acetate
  5. washwashed twice with a saturated solution of aqueous sodium hydrogenocarbonate
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customto give 0.17 g of crude material
  9. customThis product is purified by chromatography over silicagel (dichloromethane/methanol/ammonia 94/6/0.6)

Sources & evidence

ORD record
ord-af527e0033c940a795474cf01ececd63
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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