Triethylamine → HCID 17798555, compound

HRID 2186192Notes

Reaction equation

HRID 2186192 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×

Conditions

Temperature
0 °C

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° C. 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 1N 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=9:11:1) 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 1N 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=9:11:1)
  13. washwashed with water

Sources & evidence

ORD record
ord-0b04b3503f9a41e0ba15c8a85484fe91
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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