Trifluoroacetic acid → Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-

HRID 1723642Notes

Reaction equation

HRID 1723642 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:23][C:20]([F:21])([F:22])[C:17]1[CH:16]=[CH:15][C:14]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18364827tert-butyl 4-(4-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 0.52 mmol 4-(4-trifluoromethyl-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester in 2 ml dichloromethane was treated with 0.2 ml trifluoroacetic acid. The mixture was stirred at 40° C. for 3 hrs then concentrated and treated with water/NaOH and extracted with dichloromethane. The combined organic phases were washed with saturated NaCl, dried with MgSO4 and evaporated to yield the title compound. MS (m/e): 228.3 (MH+, 100%)

Workup

  1. concentrationthen concentrated
  2. additiontreated with water/NaOH
  3. extractionextracted with dichloromethane
  4. washThe combined organic phases were washed with saturated NaCl
  5. dry with materialdried with MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-58cd6dd3f0924ee499d3256960bc9e9e
Source dataset
uspto-grants-2009_02
Patent number
US07485637B2

Reaction notes

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