Sodium hydride → HCID 86721897, compound

HRID 1049054Notes

Reaction equation

HRID 1049054 reaction equation
[Br-].[CH2:2]([NH:6][S:7]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][PH3+])=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH:3]([CH3:5])[CH3:4].[H-].[Na+].[CH3:20][S:21]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)(=[O:23])=[O:22]>CN(C=O)C.CCOC(C)=O>[CH2:2]([NH:6][S:7]([C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[C:27]2[CH2:28][CH2:29][N:24]([S:21]([CH3:20])(=[O:23])=[O:22])[CH2:25][CH2:26]2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH:3]([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 120720291-(Methylsulphonyl)piperidin-4-oneHCID 86721895HCID 86721895, compound

Product 1

HCID 86721897HCID 86721897, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-isobutylsulfamoyl-benzyl-phosphonium bromide (1.87 g, 3.29 mmol) in DMF (10 mL) was treated with NaH (60% dispersion in mineral oil, 329 mg, 8.22 mmol) and stirred at room temperature for 1 hour. 1-(Methylsulfonyl)piperidin-4-one (758 mg, 4.28 mmol) was added and the mixture stirred at room temperature for 18 hours. The mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-100% EtOAc in cyclohexane) gave N-isobutyl-4-(1-methanesulfonyl-piperidin-4-ylidenemethyl)-benzenesulfonamide (392 mg, 31%). 1H NMR (300 MHz, CDCl3) δ 7.81 (d, J=8.2 Hz, 2H), 7.31 (d, J=8.2 Hz, 2H), 6.43 (s, 1H), 4.40 (t, J=6.5 Hz, 1H), 3.37 (t, J=5.7 Hz, 2H), 3.25 (t, J=5.8 Hz, 2H), 2.82-2.76 (m, 5H), 2.60 (t, J=5.7 Hz, 2H), 2.53 (t, J=5.7 Hz, 2H), 1.80-1.66 (m, 1H), 0.88 (d, J=6.7 Hz, 6H). LCMS (m/z, Method A) ES+ 523.1 [M+Na]+.

Workup

  1. stirringthe mixture stirred at room temperature for 18 hours
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customPurification by silica gel column chromatography (0-100% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-db8197ecabf647c4b5f7eb40b313250a
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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