Triethylamine → HCID 23447429, compound

HRID 1840593Notes

Reaction equation

HRID 1840593 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-12ad702c25914681b16c3e301336d44e
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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