Sodium Iodide → HCID 69426035, compound

HRID 1278966Notes

Reaction equation

HRID 1278966 reaction equation
Br[C:2]1[C:3]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:35])[CH2:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[CH:9]1([CH:3]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:8]=2)[N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:35])[CH2:27][CH2:28][C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[CH2:17][CH2:16]2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 18425707N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamideHCID 53749036HCID 53749036, compound

Product 1

HCID 69426035HCID 69426035, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.8 g (15.0 mmol) (bromocyclohexylphenyl)-methane, 4.3 g (15.0 mmol) N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide, 3.1 g (22.5 mmol) potassium carbonate and 0.22 g (1.5 mmol) sodium iodide are stirred in 40 ml DMF for two hours at ca. 105° C. After cooling, the mixture is poured into 100 ml water and extracted with 150 ml acetic acid ethyl ester. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified twice over silica gel with CHCl3/CH3OH (90/10 and 95/5) and crystallized from 10 ml acetonitrile after drawing off the solvent. Beige colored crystals with an MP of 109-110° C., yield 1.4 g (20%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 150 ml acetic acid ethyl ester
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent is removed under vacuum
  5. customThe residue is chromatographically purified twice over silica gel with CHCl3/CH3OH (90/10 and 95/5)
  6. customcrystallized from 10 ml acetonitrile

Sources & evidence

ORD record
ord-0cd2487504b84e73bb217755ba011458
Source dataset
uspto-grants-2002_09
Patent number
US06444823B1

Reaction notes

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