Sodium Iodide → HCID 21717151, compound

HRID 1386025Notes

Reaction equation

HRID 1386025 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[S:10]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)(=[O:12])=[O:11].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>C(#N)C>[C:13]1([S:10]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]2[CH2:3][CH2:2][N:40]2[CH2:41][CH2:42][N:37]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=3)[CH2:38][CH2:39]2)(=[O:12])=[O:11])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 21717133HCID 21717133, compound

Product 1

HCID 21717151HCID 21717151, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(2-chloroethyl)-1-(naphthalene-1-sulfonyl)piperidine (D1) (250 mg) in acetonitrile (20 ml) was added sodium iodide (12 mg), potassium carbonate (108 mg) and 1-(2-pyridyl)piperazine (143 ul). The mixture was heated at reflux overnight. After cooling to room temperature the residue was chromatographed on silica eluting with 5% methanol in dichloromethane to afford the title compound as an oil (301 mg, 87%). Trituration with diethyl ether afforded a foam. MH+ 465

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customwas chromatographed on silica eluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-380c17843db24593adf9019b3706709f
Source dataset
uspto-grants-2001_07
Patent number
US06265408B1

Reaction notes

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