Sodium Iodide → HCID 59063196, compound

HRID 412648Notes

Reaction equation

HRID 412648 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[C:24]([NH:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)=[O:25].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[NH3:6].[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[C:24]([NH:26][CH:27]1[CH2:28][CH2:29][N:30]([CH2:2][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH2:31][CH2:32]1)=[O:25]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 745714-(Chloromethyl)pyridineHCID 57060556HCID 57060556, compound

Product 2

HCID 222AmmoniaHCID 59063196HCID 59063196, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(Chloromethyl)pyridine (88.1 mg) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2-(4-piperidinyl)-2-piperidinecarboxamide (118 mg) [see Example 31], potassium carbonate (56.6 mg) and sodium iodide (6.7 mg) in acetonitrile (10 ml) at 0° C. The reaction mixture was then stirred at room temperature for 18 hours, after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent system of 93:7:1, by volume, dichloromethane:methanol:0.88 aqueous ammonia solution to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-[1-(4-pyridinylmethyl)-4-piperidinyl]-2-piperidinecarboxamide (14.8 mg) as a red coloured gum.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. customThe crude product was purified by column chromatography on silica gel eluting with a solvent system of 93:7:1, by volume, dichloromethane

Sources & evidence

ORD record
ord-a929923250de45409b56de643bcd4ed4
Source dataset
uspto-grants-2003_05
Patent number
US06562964B1

Reaction notes

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