Trifluoroacetic acid → 1,2,3,6-Tetrahydro-4-(3-(methylthio)phenyl)pyridine

HRID 2220095

Reaction equation

HRID 2220095 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20][CH3:21])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:21][S:20][C:16]1[CH:15]=[C:14]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 129889644-Hydroxy-4-(3-methylsulfanylphenyl)-piperidin-1-carboxylic acid tert-butyl ester

Product 1

HCID 129889651,2,3,6-Tetrahydro-4-(3-(methylthio)phenyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Hydroxy-4-(3-methylsulfanyl-phenyl)-piperidin-1-carboxylic acid tert-butyl ester (3.97 g) was dissolved in CH2Cl2 (500 ml) and trifluoroacetic acid (80 ml) was added in one portion. The mixture was refluxed for one hour and then washed with two portions of 10%-Na2CO3, dried (MgSO4), filtered and evaporated to dryness. Yield 2.07 g. MS m/z (relative intensity, 70 eV) 205 (M+, 73), 158 (44), 129 (95), 128 (80), 82 (bp).

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. washwashed with two portions of 10%-Na2CO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f3519a99f49b4cc4813845475c58d895
Source dataset
uspto-grants-2008_08
Patent number
US07417043B2

Linked notes

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