Triethylamine → HCID 68681203, compound

HRID 646881Notes

Reaction equation

HRID 646881 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:4]=1.C(N(CC)CC)C.[S:25](Cl)([CH3:28])(=[O:27])=[O:26]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:4]=1)[S:25]([CH3:28])(=[O:27])=[O:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68680582N-methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine

Product 1

HCID 68681203HCID 68681203, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine (128 mg, 0.54 mmol, as prepared in the previous step) and triethylamine (301 μL, 2.16 mmol) in 4 mL of CH2Cl2 was added mesyl chloride (125 μL, 1.62 mmol) via microsyringe and the reaction was allowed to stir overnight. At this time it was diluted with CHCl3 (50 mL), washed with satd aq NaHCO3 (2×50 mL), and dried (Na2SO4). Concentration of the solvent in vacuo and purification of the crude material using preparative TLC (4% MeOH—CHCl3) afforded 154 mg (91%) of the title compound as an oil. Mass spectrum (ESI, m/z): Calcd. for C13H19N3O4S, 314.1 (M+H), found 314.1.

Workup

  1. washwashed with satd aq NaHCO3 (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. customConcentration of the solvent in vacuo and purification of the crude material

Sources & evidence

ORD record
ord-a87ac008ec3a4f20b54ceee9345569be
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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