Triethylamine → HCID 17798555, compound

HRID 1840605Notes

Reaction equation

HRID 1840605 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]3=[O:20])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH2:29][CH:30]([C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1)[CH3:31]>ClCCl>[C:30]([C:32]1[CH:37]=[CH:36][C:35]([S:38]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH:10]3[CH2:11][CH2:12][N:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH2:8][CH2:9]3)[C:15](=[O:20])[CH2:16]2)(=[O:40])=[O:39])=[CH:34][CH:33]=1)([CH3:31])=[CH2:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10858694HCID 10858694, compoundHCID 23447513HCID 23447513, compound

Product 1

HCID 17798555HCID 17798555, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1-[1-(4-pyridyl)-4-piperidylmethyl]-2-piperazinone (549 mg) and triethylamine (0.836 ml) in dichloromethane (10 ml) was added dropwise a solution of 4-(2-bromo-1-methylethyl)benzenesulfonyl chloride (893 mg) in dichloromethane (2 ml) at 0° C., and the mixture was stirred at 0 for 1 hour and then at room temperature for 6 hours. The reaction solution was diluted with dichloromethane, washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was dissolved in ethanol (20 ml), and to the solution was added 1 N sodium hydroxide (2 ml). The mixture was stirred at 80° C. for 30 minutes, and to the reaction solution was added ethyl acetate. The mixture was washed with water and saturated brine, dried (MgSO4) and concentrated, and the residue was purified with silica gel column chromatography (acetone:methanol=9:1→1:1) and washed with water to give colorless crystals of 4-(4-isopropenylbenzenesulfonyl)-1-[1-(4-pyridyl)-4-piperidylmethyl]-2-piperazinone (155 mg).

Workup

  1. waitat room temperature for 6 hours
  2. washwashed with water and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethanol (20 ml)
  6. additionto the solution was added 1 N sodium hydroxide (2 ml)
  7. stirringThe mixture was stirred at 80° C. for 30 minutes
  8. additionto the reaction solution was added ethyl acetate
  9. washThe mixture was washed with water and saturated brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customthe residue was purified with silica gel column chromatography (acetone:methanol=9:1→1:1)
  13. washwashed with water

Sources & evidence

ORD record
ord-541a6c02d48f4f03bcea13fa87da6b1f
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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