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

HRID 1520674Notes

Reaction equation

HRID 1520674 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.C([O-])(O)=O.[Na+]>[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

8

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 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

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 heated at reflux for 18 hours and upon cooling was diluted with ethyl acetate (200 mL) and aqueous NaHCO3. The crude product was isolated by concentration of the organic layer and was purified on silica gel, which was eluted with 5% methanolic ammonia in methylene chloride to give the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperatureupon cooling
  4. customThe crude product was isolated by concentration of the organic layer
  5. customwas purified on silica gel, which
  6. washwas eluted with 5% methanolic ammonia in methylene chloride

Sources & evidence

ORD record
ord-27922007bd3846fbb38643b9aac79f06
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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