Trifluoroacetic acid → 4-(4-Phenoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 1759767Notes

Reaction equation

HRID 1759767 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[O:21]([C:18]1[CH:19]=[CH:20][C:15]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:16][CH:17]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 22600006HCID 22600006, compound

Product 1

HCID 225999894-(4-Phenoxyphenyl)-1,2,3,6-tetrahydropyridineYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 3 ml of methylene chloride solution of 772 mg of N-tert-butoxycarbonyl-4-(4-phenoxyphenyl)-4-piperidinol synthesized in Step A, a 3 ml of trifluoroacetic acid was dropwise added under ice cooling. The resultant mixture was stirred at room temperature for 2-hours, then adjusted by 10% aqueous sodium hydroxide solution to pH=9 to 10 and extracted with ether. The extract was dried, filtered, then concentrated under reduced pressure to give a residue, which was then recrystallized from ether/methylene chloride to give 4-(4-phenoxyphenyl)-1,2,3,6-tetrahydropyridine in an amount of 250 mg (yield 47%).

Workup

  1. extractionextracted with ether
  2. customThe extract was dried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue, which
  6. customwas then recrystallized from ether/methylene chloride

Sources & evidence

ORD record
ord-b6bae97fc9bd41a5887bd983ac4d17e3
Source dataset
uspto-grants-2005_01
Patent number
US06838470B2

Reaction notes

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