Triethylamine → 1-((3-Chloropropyl)sulfonyl)-4-methylpiperazine

HRID 536224Notes

Reaction equation

HRID 536224 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CCN(CC)CC>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([N:13]1[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]1)(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 531671-Methylpiperazine

Product 1

HCID 102433851-((3-Chloropropyl)sulfonyl)-4-methylpiperazineYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Chloropropanesulfonyl chloride (1.0 g, 5.6 mmol) dissolved in CH2Cl2 (20 mL) and cooled to ˜0° C. was treated dropwise with a solution of 1-methylpiperazine (566 mg, 5.6 mmol) and Et3N (572 mg, 5.6 mmol) in CH2Cl2 (10 mL). Following complete addition, the mixture was allowed to warm to rt and stir an additional 2 h. The solvent was evaporated under reduced pressure, the residue triturated with EtOAc (30 mL), vacuum filtered and the solid washed well with EtOAc. The filtrate was concentrated under reduced pressure and the oil residue dried under high vacuum to give the title compound (1.27 g, 93%): 1H NMR (CDCl3) δ: 2.17-2.26 (2H, m), 2.49 (3H, s), 2.75-2.77 (4H, m), 3.02-3.07 (2H, m), 3.46-3.49 (4H, m), 3.60 (2H, t).

Workup

  1. additionaddition
  2. temperatureto warm to rt
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue triturated with EtOAc (30 mL), vacuum
  5. filtrationfiltered
  6. washthe solid washed well with EtOAc
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe oil residue dried under high vacuum

Sources & evidence

ORD record
ord-2ead914774a94f6fbc79afe6201df3d6
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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