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

HRID 1483910

Reaction equation

HRID 1483910 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-8ea3ec1ca05045deb71ab743ec5eb24c
Source dataset
uspto-grants-2016_08
Patent number
USRE046117E1

Linked notes

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