Piperidine → HCID 10971939, compound

HRID 1596057Notes

Reaction equation

HRID 1596057 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:35])[CH2:16][CH2:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]=3[C:29]([O:31]CC=C)=[O:30])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1CCCCC1>ClCCl.Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([C:15](=[O:35])[CH2:16][CH2:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]=3[C:29]([OH:31])=[O:30])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 11776TriphenylphosphineHCID 10928704HCID 10928704, compound

Product 1

HCID 10971939HCID 10971939, compoundYield 107.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 11F (200 mg, 0.431 mmol) in dichloromethane (5 mL) at room temperature was treated with tetrakis(triphenylphosphine)palladium (43 mg, 0.0375 mmol), triphenylphosphine (19.6 mg, 0.075 mmol), piperidine (0.0447 mL, 0.452 mmol), and allowed to stir at room temperature for 30 minutes. The reaction mixture was diluted with 0.5 N HCl, and extracted with dichloromethane. The organic layer was dried (Na2SO4), filtered, concentrated, and purified on silica gel with 10% methanol/CH2Cl2 to provide 197 mg (100%) of the desired compound as an white solid.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on silica gel with 10% methanol/CH2Cl2

Sources & evidence

ORD record
ord-4eeef9b9f37b42d080cddf34d52f276a
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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