Dimethyl Sulfoxide → (4-Chloro-2-nitro-phenyl)-(tetrahydro-pyran-4-ylmethyl)-amine

HRID 469722Notes

Reaction equation

HRID 469722 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1CN.[CH:20]([N:23](CC)C(C)C)(C)C.CS(C)=O>O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:23][CH2:20][CH:15]2[CH2:14][CH2:13][O:12][CH2:17][CH2:16]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 676604-Chloro-1-fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 97924(Tetrahydro-2H-pyran-2-ylmethyl)amine

Product 1

HCID 62349965(4-Chloro-2-nitro-phenyl)-(tetrahydro-pyran-4-ylmethyl)-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Fluoro-5-chloronitrobenzene (0.762 g; 4.341 mmol), tetrahydropyran methyl amine (0.5 g; 4.341 mmol), N,N-diisopropylethylamine (0.756 mL; 4.341 mmol) and dimethylsulfoxide (2 mL) are heated at 80° C. in an oil bath for 4 days. After this time the reaction is cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined organics are washed with water and brine and concentrated in vacuo to afford title compound as an orange oil which solidified upon standing and was used crude in subsequent reactions. ESI m/z 271 [M+H]+

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics are washed with water and brine
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89dc874623a046eaae6bc77ca6bbdc58
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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