Methanesulfonyl chloride → 4-Ethyl-N-hexyl-4-(3-methanesulfonylaminophenyl)piperidine

HRID 397710Notes

Reaction equation

HRID 397710 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.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[NH3:1].[CH2:20]([C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:23]([CH3:22])(=[O:25])=[O:24])[CH:3]=2)[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]1)[CH3:21]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 230009254-(3-aminophenyl)-4-ethyl-N-hexylpiperidine

Product 2

HCID 222AmmoniaHCID 230009654-Ethyl-N-hexyl-4-(3-methanesulfonylaminophenyl)piperidineYield 62.7%

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 methanesulfonyl chloride (0.2 ml, 1.18 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 (40:60:1), then ethyl acetate:0.880 ammonia (100:1) and then methanol:ethyl acetate:0.880 ammonia (10:89:1) to give the title compound as an oil (20 mg, 29%).

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-bc32e551ea1046af9fec9947b25d66ad
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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