Triethylamine → HCID 23447465, compound

HRID 1840591Notes

Reaction equation

HRID 1840591 reaction equation
Cl.[C:2]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][C:10]2=[O:15])=[CH:6][CH:5]=1)#[N:3].C(N(CC)CC)C.Cl[CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([S:28]([CH:27]=[CH2:26])(=[O:30])=[O:29])[CH2:11][C:10]2=[O:15])=[CH:16][CH:17]=1)#[N:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 23447422HCID 23447422, compound

Product 1

HCID 23447465HCID 23447465, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-cyanobenzyl)-2-piperazinone hydrochloride (3.85 g) and triethylamine (12.5 ml) in dichloromethane (50 ml) was added dropwise a solution of 2-chloroethanesulfonyl chloride (4.08 g) in dichloromethane (10 ml) at 0° C., and the mixture was stirred at 0° C. for 4 hours. The reaction solution was diluted with dichloromethane, washed with sodium bicarbonate solution and saturated brine, dried (MgSO4) and concentrated, and the residue was purified with silica gel column chromatography (ethyl acetate) to give colorless crystals of 1-(4-cyanobenzyl)-4-vinylsulfonyl-2-piperazinone (3.15 g).

Workup

  1. washwashed with sodium bicarbonate solution and saturated brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customthe residue was purified with silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-fe0ae50e4ddb4714a080ddae04228aae
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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