HCID 68911328, compound → HCID 68909667, compound

HRID 657646Notes

Reaction equation

HRID 657646 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25]([OH:27])=O)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>S(Cl)(Cl)(=O)=O>[N:1]1([C:25]([CH:24]=[CH:23][C:20]2[CH:19]=[CH:18][C:17]([C:14]3[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:12][CH:13]=3)=[CH:22][CH:21]=2)=[O:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 68911328HCID 68911328, compound

Product 1

HCID 68909667HCID 68909667, compoundYield 141.9%

Reagents, catalysts & solvents 1

HCID 24648Sulfuryl chlorideSolvent

Procedure

A solution of 3-[4′-(3-piperidinopropoxy)biphenyl-4-yl]acrylic acid (1 g) in sulfonyl chloride (5 mL) is stirred at a temperature close to 40° C. for two hours, then concentrated under reduced pressure. The concentrate is dissolved in dichloromethane (10 mL) and piperidine (4 mL) is added dropwise. The mixture is stirred at room temperature for one hour, washed with water, then a normal aqueous solution of hydrochloric acid, dried over magnesium sulfate, concentrated and purified by chromatography over silica gel using a gradient dichloromethane/methanol from 100/0 to 95/5. Fractions containing the expected product are pooled and concentrated under reduced pressure to afford 840 mg of 1-(3-{[4′-(2-piperidinocarbonylethen-1-yl)biphenyl-4-yl]oxy}propyl)piperidine as beige crystals melting at 146-150° C.

Workup

  1. customclose to 40° C. for two hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe concentrate is dissolved in dichloromethane (10 mL)
  4. additionpiperidine (4 mL) is added dropwise
  5. washwashed with water
  6. dry with materiala normal aqueous solution of hydrochloric acid, dried over magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by chromatography over silica gel using a gradient dichloromethane/methanol from 100/0 to 95/5
  9. additionFractions containing the expected product
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac8627eb7f65463dbdae634458c973fa
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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