Trifluoroacetic acid → N-Ethyl-4-methoxy-N-piperidin-4-yl-benzenesulfonamide

HRID 2354047Notes

Reaction equation

HRID 2354047 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:26][CH3:27])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:26]([N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[S:15]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)(=[O:16])=[O:17])[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 686888764-[Ethyl-(4-methoxy-benzenesulfonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58816568N-Ethyl-4-methoxy-N-piperidin-4-yl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-[ethyl-(4-methoxy-benzenesulfonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (11.1 g, 28 mmol) in CH2Cl2 (50 mL) is cooled at 0° C. and TFA (40 mL) is added. The mixture is stirred at 0° C. for 0.5 h and then evaporated. The residue is dissolved in CH2Cl2 (50 mL) and 1 M aq. NaOH (50 mL) is added. The mixture is stirred for 15 h at r.t., then the phases are separated and the aq. phase is extracted with CH2Cl2 (4×30 mL). The combined org. phases are washed with 1 M aq. NaOH (2×30 mL), dried (Na2SO4), filtered and evaporated to provide the title compound.

Workup

  1. customevaporated
  2. dissolutionThe residue is dissolved in CH2Cl2 (50 mL)
  3. addition1 M aq. NaOH (50 mL) is added
  4. stirringThe mixture is stirred for 15 h at r.t.
  5. customthe phases are separated
  6. extractionthe aq. phase is extracted with CH2Cl2 (4×30 mL)
  7. washphases are washed with 1 M aq. NaOH (2×30 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-87786024dee54810888c896298613072
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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