Potassium Iodide → N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide

HRID 466363Notes

Reaction equation

HRID 466363 reaction equation
[I-].[K+].Br[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1.[CH2:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:18]>CN(C=O)C>[CH2:17]([N:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1)[CH3:18]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 480381-Heptanamine, N-ethyl-HCID 21182029N-[4-(2-bromoethyl)phenyl]methanesulfonamide

Product 1

HCID 53740092N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of potassium iodide (4.15 g, 0.025 mol), N-[4-(2-bromoethyl)phenyl]methanesulfonamide as prepared in Preparation 5 above (7.0 g, 0.025 mol), ethylheptylamine (7.16 g, 0.05 mol) and 120 ml of DMF, under N2, is allowed to stir at ambient temperature. After 18 hours the reaction mixture is concentrated under reduced pressure and the residue is combined with cold dilute NaOH. The alkaline mixture is extracted with Et2O, neutralized to pH 7 with dilute HCl and extracted with CH2Cl2. The CH2Cl2 extracts are concentrated and the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2 to give N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide, a gum. MS calc'd for C18H32N2O2S (M+): 340.2184. Found: 340.2170.

Workup

  1. concentrationAfter 18 hours the reaction mixture is concentrated under reduced pressure
  2. extractionThe alkaline mixture is extracted with Et2O
  3. extractionextracted with CH2Cl2
  4. concentrationThe CH2Cl2 extracts are concentrated
  5. customthe residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2

Sources & evidence

ORD record
ord-abc603748967472d81efdda457d933aa
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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