Dichloromethane → 2-[(1-Methyl-1-piperidin-4-ylethyl)sulfonyl]-6-(trifluoromethyl)pyridine

HRID 1873850Notes

Reaction equation

HRID 1873850 reaction equation
[CH3:1][C:2]([CH:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1)([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[N:8]=1)(=[O:6])=[O:5])[CH3:3].FC(F)(F)C(O)=O.ClCCl>C(OCC)(=O)C>[CH3:3][C:2]([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:15])([F:16])[F:14])[N:8]=1)(=[O:6])=[O:5])([CH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1)[CH3:1]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59447129Tert-butyl 4-(1-methyl-1-{[6-(trifluoromethyl)pyridin-2-yl]sulfonyl}ethyl)piperidine-1-carboxylate

Product 1

HCID 594474312-[(1-Methyl-1-piperidin-4-ylethyl)sulfonyl]-6-(trifluoromethyl)pyridineYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 25 ml round bottom flask was added tert-butyl 4-(1-methyl-1-{[6-(trifluoromethyl)pyridin-2-yl]sulfonyl}ethyl)piperidine-1-carboxylate (0.806 g, 1.85 mmol), trifluoroacetic acid (1.5 ml) and dichloromethane (5 ml). The resulting solution was stirred at room temperature for 1 hour. It was diluted with 50 ml ethyl acetate, washed with 50 ml 10% KOH and then 30 ml brine. The organics were dried over sodium sulfate, filtered and concentrated to give 0.33 g desired product as cyrstalline solid.

Workup

  1. washwashed with 50 ml 10% KOH
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f4275c3e1294583a6bb777b997e86bc
Source dataset
uspto-grants-2012_11
Patent number
US08304434B2

Reaction notes

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