Sodium Iodide → HCID 136119447, compound

HRID 2218262Notes

Reaction equation

HRID 2218262 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:21])[CH2:18][CH2:19]Cl)[CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])[N:3]=1.[I-].[Na+].[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C(#N)C.O>[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:21])[CH2:18][CH2:19][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])[N:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8082PiperidineHCID 136336335HCID 136336335, compound

Product 1

HCID 136119447HCID 136119447, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of N-{3-[2-amino-3-(hydroxymethyl)-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-3-chloropropanamide (0.065 g, 0.16 mmol) and sodium iodide (0.007 g, 0.05 mmol) in acetonitrile (5 mL) was added piperidine (0.16 mL, 1.63 mmol), and the mixture was stirred at 75° C. overnight. After cooled to room temperature, the resulting mixture was diluted with water and extracted with ethyl acetate. The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica-gel (chloroform:methanol, 85:15) to give N-{3-[2-amino-3-(hydroxymethyl)-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-3-(1-piperidinyl)propanamide as a white foam (0.055 g, yield 75%).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica-gel (chloroform:methanol, 85:15)

Sources & evidence

ORD record
ord-df48889814c3433d854a343b22d28e7f
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

Loading…