Diisopropylethylamine → 4-(1-Cyclopropylpiperidin-4-ylamino)-3-nitrobenzenesulfonamide

HRID 573063Notes

Reaction equation

HRID 573063 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH:15]1([N:18]2[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]2)[CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>O1CCCC1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH:15]1([N:18]2[CH2:23][CH2:22][CH:21]([NH:24][C:2]3[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=3[N+:12]([O-:14])=[O:13])[CH2:20][CH2:19]2)[CH2:17][CH2:16]1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 162276441-Cyclopropylpiperidin-4-amineHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 260427514-(1-Cyclopropylpiperidin-4-ylamino)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-3-nitrobenzenesulfonamide (1.26 g) and 1-cyclopropylpiperidin-4-amine (0.802 g) in tetrahydrofuran (20 mL) was added N,N-diisopropylethylamine (2.22 g) and 4-dimethylaminopyridine (35 mg). The mixture was stirred at reflux overnight. The mixture was diluted with ethyl acetate (200 mL) and washed with aqueous NaHCO3, water, and brine and dried over Na2SO4. After filtration and concentration, the residue was dissolved in dichloromethane and loaded on a column and eluted with dichloromethane (500 mL), 5% 7N NH3 in 10% methanol in dichloromethane (1.5 L) to give the product.

Workup

  1. temperatureat reflux overnight
  2. washwashed with aqueous NaHCO3, water, and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washeluted with dichloromethane (500 mL), 5% 7N NH3 in 10% methanol in dichloromethane (1.5 L)
  7. customto give the product

Sources & evidence

ORD record
ord-f0bd433cf5894caba967378264476c30
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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