Triethylamine → HCID 23447429, compound

HRID 2186181Notes

Reaction equation

HRID 2186181 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:25][CH2:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[Cl:25][CH2:26][S:27]([N:12]1[CH2:13][CH2:14][N:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:17][CH:16]=2)[C:10](=[O:15])[CH2:11]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77054(Chloromethyl)sulfonyl chlorideHCID 23447422HCID 23447422, compound

Product 1

HCID 23447429HCID 23447429, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-cyanobenzyl)-2-piperazinone hydrochloride (3.78 g) and triethylamine (6.27 ml) in dichloromethane (50 ml) was added a solution of chloromethanesulfonyl chloride (2.68 g) in dichloromethane (10 ml) at 0° C., and the mixture was stirred at 0° C. for 1 hour. 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 (hexane:ethyl acetate=1:2) to give colorless crystals of 4-chloromethylsulfonyl-1-(4-cyanobenzyl)-2-piperazinone (4.01 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 (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-f997cb9af5bf4befa0f23e296b93be39
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

Loading…