Ethanesulfonyl chloride → 4-(3-Ethanesulfonylaminophenyl)-4-ethyl-N-hexylpiperidine

HRID 397711Notes

Reaction equation

HRID 397711 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:20][CH3:21])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:22]([S:24](Cl)(=[O:26])=[O:25])[CH3:23]>N1C=CC=CC=1>[NH3:1].[CH2:22]([S:24]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:20][CH3:21])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1)(=[O:26])=[O:25])[CH3:23]

Participants

5

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 230009254-(3-aminophenyl)-4-ethyl-N-hexylpiperidine

Product 2

HCID 222AmmoniaHCID 230010464-(3-Ethanesulfonylaminophenyl)-4-ethyl-N-hexylpiperidineYield 66.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4-(3-aminophenyl)-4-ethyl-N-hexylpiperidine (Preparation 64, 50.0 mg, 0.174 mmol) in anhydrous pyridine (4 ml) under nitrogen at 0° C. was added ethanesulfonyl chloride (0.2 ml, 1.15 mmol). The solution was stirred at room temperature for 48 h. Ice (5 g) was added and, after 30 min, the reaction mixture was extracted with dichloromethane (10 ml). The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to give the crude product which was purified by silica (5 g) column chromatography, eluting with ethyl acetate:hexane:0.880 ammonia (50:50:1) and then methanol:ethyl acetate:0.880 ammonia (10:89:1) to give the title compound as an oil (22 mg, 30%).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane (10 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product which
  7. customwas purified by silica (5 g) column chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-893c80ffaf0c4b40b859ef1bc47a35cb
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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