Pyridine → HCID 18357136, compound

HRID 427443Notes

Reaction equation

HRID 427443 reaction equation
N1C=CC=CC=1.[N:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)#[N:20]>ClCCl.C(N(CC)CC)C>[N:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:14][CH2:15][N:16]([S:27]([C:24]3[CH:23]=[CH:22][C:21]([C:19]#[N:20])=[CH:26][CH:25]=3)(=[O:29])=[O:28])[CH2:17][CH2:18]2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 705171-(4-Pyridyl)piperazine

Product 1

HCID 18357136HCID 18357136, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Pyridine (1 ml) was added to a solution of 1-(4-pyridyl)piperazine (0.33 g) in dry dichloromethane (20 ml) and triethylamine (1 ml) at 5° C. The reaction mixture was treated with 4-cyanobenzenesulphonyl chloride (0.40 g). The reaction mixture was then stirred under argon for 4 hours allowing to warm to room temperature. The dichloromethane solvent was removed by evaporation and the residual pyridine solution poured into aqueous sodium hydrogen carbonate solution and then extracted with ethyl acetate. The organic extracts were then washed with aqueous sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to yield a pale cream solid which was then recrystallised from ethyl acetate isohexane to give 1-(4-pyridyl)-4-(4-cyanophenylsulphonyl)piperazine (0.31 g) as a solid. m.p. 212-213° C.; microanalysis, found: C, 58.8; H, 4.9; N, 17.1%; C16H16N4O2S requires: C, 8.5: H, 4.91; N, 17.1%; NMR: (CDCl3) 3.18(t,4H), 3.44(t,4H), 6.62(dd,2H), 7.88(q,4H), 8.30(dd,2H); MS: m/z 329 (MH)+.

Workup

  1. customThe dichloromethane solvent was removed by evaporation
  2. additionthe residual pyridine solution poured into aqueous sodium hydrogen carbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were then washed with aqueous sodium hydrogen carbonate solution, water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto yield a pale cream solid which
  8. customwas then recrystallised from ethyl acetate isohexane

Sources & evidence

ORD record
ord-8c46a7b2e14944a5910a2c702b4125dc
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

Loading…