Pyridine → HCID 44335571, compound

HRID 1519672Notes

Reaction equation

HRID 1519672 reaction equation
S(Cl)(C1C=CC(C)=CC=1)(=O)=[O:2].[N:12]1[CH:17]=[CH:16]C=[CH:14][CH:13]=1.O[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[N:12]1([CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[CH2:17][CH2:16][O:2][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 13796792HCID 13796792, compound

Product 1

HCID 44335571HCID 44335571, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

TsCl (12 g) and pyridine (10 mL) were added to a chloroform (0.1 L) solution of 4′-(3-hydroxypropoxy)biphenyl-4-carbonitrile (5.1 g) as obtained in Example 4-(1), and the mixture was stirred overnight at room temperature. Chloroform was added to the reaction mixture, and the mixture was washed with a 1.0 mol/L hydrochloric acid aqueous solution and a 1.0 mol/L sodium hydrogen carbonate aqueous solution. After the organic layer was dried over anhydrous magnesium sulfate, the desiccant was filtered out, and the solvent was distilled off under reduced pressure. IPE was added to the resulting residue, and the precipitated solid was collected by filtration. Then, ethanol (40 mL) and morpholine (8.8 mL) were added, and the mixture was stirred for 1 hour at 80° C. The reaction mixture was distilled under reduced pressure, and the resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=50/50→90/10) to obtain 4′-[3-(morpholin-4-yl)propoxy]biphenyl-4-carbonitrile (light brown solid) (5.1 g, 79%).

Workup

  1. washthe mixture was washed with a 1.0 mol/L hydrochloric acid aqueous solution
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccant was filtered out
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionIPE was added to the resulting residue
  6. filtrationthe precipitated solid was collected by filtration
  7. additionThen, ethanol (40 mL) and morpholine (8.8 mL) were added
  8. stirringthe mixture was stirred for 1 hour at 80° C
  9. distillationThe reaction mixture was distilled under reduced pressure
  10. customthe resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=50/50→90/10)

Sources & evidence

ORD record
ord-efe3eb3ae0fd4f768ddc566fb009f3c7
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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