1-Propanol → HCID 86680283, compound

HRID 2202578Notes

Reaction equation

HRID 2202578 reaction equation
[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25](Cl)=[N:26][CH:27]=2)[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](=[O:32])([O-])[O-:30].[K+].[K+].[CH2:35](O)[CH2:36][CH3:37]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O>[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:29]([O:30][CH2:35][CH2:36][CH3:37])=[O:32])=[N:26][CH:27]=2)[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10311-PropanolHCID 11430Potassium CarbonateHCID 86680284HCID 86680284, compound

Product 1

HCID 86680283HCID 86680283, compound

Reagents, catalysts & solvents 3

HCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 721 mg of 5-(4-benzhydryloxypiperidin-1-ylmethyl)-2-chloropyridine synthesized in Production Example 36, 21 mg of palladium acetate, 41 mg of 1,3-bis(diphenylphosphino)propane, 380 mg of potassium carbonate, 7.0 mL of n-propanol, and 3.5 mL of N,N-dimethylformamide was stirred under a carbon monoxide atmosphere at an external temperature of 90° C. for 7 hours. After the solvent was distilled off, the mixture was diluted with ethyl acetate. The resulting mixture was thrown into water, and the organic layer was collected by separation. The organic layer was washed with a saturated saline solution and then dried over magnesium sulfate. After the solvent was distilled off, the resulting product was subjected to a p-TLC to give the title compound (569 mg).

Workup

  1. distillationAfter the solvent was distilled off
  2. additionthe mixture was diluted with ethyl acetate
  3. customthe organic layer was collected by separation
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-cf423846d66f4feebc687c1f9ff5682d
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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