Triethylamine → 1-(Methanesulfonyl)-4-methylpiperazine

HRID 1090351Notes

Reaction equation

HRID 1090351 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:16]([CH3:15])(=[O:18])=[O:17])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 531671-Methylpiperazine

Product 1

HCID 8177701-(Methanesulfonyl)-4-methylpiperazine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-methylpiperazine (3.0 g, 29.9 mmol), triethylamine (3.6 g, 35.9 mmol) and methanesulfonyl chloride (Compound 19, 4.11 g, 35.9 mmol) in tetrahydrofuran (20 ml) was stirred at 0° C. for 2 hours. The mixture was filtered and the filtrate was evaporated to dryness to give a solid. The solid was redissolved in ethyl acetate and washed with water. Evaporation of the dried (magnesium sulfate) organic phase gave the title sulfonamide. 1HNMR(CDCl3): 2.35 (s, 3H), 2.53 (t, 4H, J=5.0 Hz), 2.79 (s, 3H) and 3.27 (t, 4H, J=5.0 Hz).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customto give a solid
  4. washwashed with water
  5. customEvaporation of the
  6. dry with materialdried (magnesium sulfate) organic phase

Sources & evidence

ORD record
ord-64a6c1fc458b4e65b8b1b9e06ea89865
Source dataset
uspto-grants-1992_01
Patent number
US05081261

Reaction notes

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