Triethylamine → HCID 69606752, compound

HRID 859929Notes

Reaction equation

HRID 859929 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 177501621-(5-Iodopyridin-2-yl)piperazine

Product 1

HCID 69606752HCID 69606752, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-(5-iodopyridin-2-yl)piperazine (CAS number 219635-89-9, 5.083 g, 17.6 mmol), and triethylamine (4.91 mL, 35.2 mmol) in CH2Cl2 (75 mL) at 0° C. was added methane sulfonyl chloride (2.04 mL, 26.4 mmol) dropwise and the resulting suspension stirred for 30 mins at room temperature. The reaction mixture was diluted with CH2Cl2 (200 mL) and washed twice with water (2×200 mL). The organic phase was washed with saturated brine solution (1×200 mL), dried (MgSO4), filtered and concentrated in vacuo to give a dark yellow solid. This was triturated with ether, filtered and dried to give 1-(5-iodopyridin-2-yl)-4-(methylsulfonyl)piperazine as a yellow solid (5.378 g, 83%).

Workup

  1. washwashed twice with water (2×200 mL)
  2. washThe organic phase was washed with saturated brine solution (1×200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a dark yellow solid
  7. customThis was triturated with ether
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-2294b91730e04387ad4b48693e1bc68b
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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