Sodium Iodide → HCID 57708849, compound

HRID 606511Notes

Reaction equation

HRID 606511 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:7])=[O:6].[OH:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:23]([C:22]1[CH:21]=[C:20]([O:19][CH2:2][CH2:3][CH2:4][S:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:7])=[O:6])[CH:27]=[CH:26][CH:25]=1)#[N:24]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 43654485HCID 43654485, compound

Product 1

HCID 57708849HCID 57708849, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of ethyl 1-[(3-chloropropyl)sulfonyl]piperidine-2-carboxylate obtained in Reference Example 97 (2.00 g, 6.72 mmol), 3-hydroxybenzonitrile (0.800 g, 6.72 mmol), potassium carbonate (0.928 g, 6.72 mmol) and sodium iodide (0.101 g, 0.672 mmol) in DMF (20 mL) was stirred at 100° C. for 51 hr. The reaction mixture was diluted with ethyl acetate, washed with water, 0.5N aqueous sodium hydroxide solution, 0.1N aqueous sodium hydroxide solution and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized from methanol to give the title compound as a pale-yellow powder (1.34 g, 52%).

Workup

  1. washwashed with water, 0.5N aqueous sodium hydroxide solution, 0.1N aqueous sodium hydroxide solution and saturated brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-814480626f834bc0b42ce48903862a45
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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