Sodium Iodide → HCID 58992705, compound

HRID 602175Notes

Reaction equation

HRID 602175 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.[I-].[Na+]>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][O:15][C:19]2[S:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 119872-ChlorobenzothiazoleHCID 24758Sodium hydrideHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 58992705HCID 58992705, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(tert-Butoxycarbonyl)piperidin-3-ylmethanol (300 mg, 1.39 mmol) was dissolved in N,N-dimethylformamide (5 mL). While this solution was chilled in an ice bath, 60% sodium hydride in oil (83.6 mg, 2.09 mmol) was added. The reaction mixture was stirred for 10 min while ice-chilled and for another 10 min at room temperature. 2-chlorobenzothiazole (0.344 mL, 2.78 mmol) and sodium iodide (208 mg, 1.39 mmol) were then added and the mixture was stirred at room temperature for 5 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract washed with brine. The washed product was then dried over magnesium sulfate and the solvent was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 460 mg (95%) of the desired compound as a colorless powder.

Workup

  1. temperatureWhile this solution was chilled in an ice bath
  2. stirringthe mixture was stirred at room temperature for 5 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract washed with brine
  5. dry with materialThe washed product was then dried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)

Sources & evidence

ORD record
ord-967507fd5a884f37b5ace21e21afcf0a
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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