Methyl iodide → HCID 69179594, compound

HRID 1071942Notes

Reaction equation

HRID 1071942 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].I[CH3:26]>>[CH3:26][N:13]([CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[S:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)(=[O:11])=[O:12]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 17644404HCID 17644404, compound

Product 1

HCID 69179594HCID 69179594, compoundYield 79.4%

Procedure

4-Nitro-N-(3-piperidinopropyl)benzenesulphonamide (Method 14; 1 g, 3.06 mmol) was stirred under nitrogen at ambient temperature. Sodium hydride (60% dispersion in mineral oil) (122 mg, 3.05 mmol) was added in portions. The reaction was stirred for 10 minutes, then iodomethane (210 μl, 3.38 mmol) was added dropwise. After 2 hours, added extra sodium hydride (<30 mg) was added, and the reaction was stirred for 15 minutes, then stood overnight. Volatiles were removed by evaporation, water (20 ml) was added and the solution was extracted with ethyl acetate (2×30 ml). The organic layers were combined, washed with water and the volatiles evaporated to give the title compound (830 mg). NMR: 1.34 (m, 2H), 1.45 (m, 4H), 1.60 (quintet, 2H), 2.19 (m, 2H), 2.24 (m, 4H), 2.72 (s, 3H), 3.02 (t, 2H), 8.02 (d, 2H), 8.40 (d, 2H); m/z: 342.

Workup

  1. waitAfter 2 hours
  2. additionwas added
  3. stirringthe reaction was stirred for 15 minutes
  4. waitstood overnight
  5. customVolatiles were removed by evaporation, water (20 ml)
  6. additionwas added
  7. extractionthe solution was extracted with ethyl acetate (2×30 ml)
  8. washwashed with water
  9. customthe volatiles evaporated

Sources & evidence

ORD record
ord-3230ed6a5ba144b0aedcf8449b35ded6
Source dataset
uspto-grants-2005_06
Patent number
US06908920B2

Reaction notes

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