Triphenylphosphine → 5-[(1-Methyl-4-piperidinyl)oxy]-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623773Notes

Reaction equation

HRID 1623773 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C:16]1[CH:17]=[CH:18][C:19]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:20]([CH:30]=1)[C:21]([NH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:22].[CH3:39][N:40]1[CH2:45][CH2:44][CH:43](O)[CH2:42][CH2:41]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1>[CH3:39][N:40]1[CH2:45][CH2:44][CH:43]([O:15][C:16]2[CH:17]=[CH:18][C:19]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[C:20]([CH:30]=2)[C:21]([NH:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[O:22])[CH2:42][CH2:41]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 5363146Diisopropyl azodicarboxylateHCID 513575145-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Product 1

HCID 513575165-[(1-Methyl-4-piperidinyl)oxy]-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
115 °C

Procedure

A solution of DIAD (0.30 ml, 1.56 mmol) in toluene (1 ml) was added dropwise to a solution of 5-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 29; 200 mg, 0.624 mmol), 1-methyl-4-piperidinol (79 mg, 0.687 mmol) and Ph3P (409 mg, 1.561 mmol) in toluene under nitrogen at 0° C. The reaction mixture was stirred at 115° C. overnight. The mixture was then cooled and concentrated. The residue was added to water and extracted with ethyl acetate (3×60 ml). The organic phase was washed with saturated brine (30 ml), dried over sodium sulphate and evaporated in vacuo to give the crude product. The crude product was purified by Pre-TCL (DCM:methanol=8:1) to yield the title compound as a yellow solid. 36 mg.

Workup

  1. temperatureThe mixture was then cooled
  2. concentrationconcentrated
  3. additionThe residue was added to water
  4. extractionextracted with ethyl acetate (3×60 ml)
  5. washThe organic phase was washed with saturated brine (30 ml)
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo
  8. customto give the crude product
  9. customThe crude product was purified by Pre-TCL (DCM:methanol=8:1)

Sources & evidence

ORD record
ord-5a81a0a6744744b895401e240d469f09
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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