Sodium Iodide → HCID 59063196, compound

HRID 841930Notes

Reaction equation

HRID 841930 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-5787deebb9e04a5287f3bd314a01af22
Source dataset
uspto-grants-2002_04
Patent number
US06372736B1

Reaction notes

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