1-Chloroethyl chloroformate → cis-1-(3-Cyanobenzenesulphonyl)-2,6-dimethylpiperazine

HRID 1064597Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([S:9]([N:12]2[C@H:17]([CH3:18])[CH2:16][N:15](CC3C=CC=CC=3)[CH2:14][C@@H:13]2[CH3:26])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].ClC(OC(Cl)C)=O>ClCCCl>[C:1]([C:3]1[CH:4]=[C:5]([S:9]([N:12]2[C@H:17]([CH3:18])[CH2:16][NH:15][CH2:14][C@@H:13]2[CH3:26])(=[O:10])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of the product from step (i) (1 g) in 1,2-dichloroethane (10 ml) was treated with 1-chloroethyl chloroformate (0.44 ml). The mixture was heated at 80° C. for 16 h. The solvents were then evaporated under reduced pressure and the residue dissolved in methanol (50 ml). The mixture then heated at 50° C. for 1 h. The solvents were then evaporated under reduced pressure. Purification was by trituration with ethyl acetate and filtration to give the subtitle compound as a white solid. Yield: 0.85 g

Workup

customThe solvents were then evaporated under reduced pressure
dissolutionthe residue dissolved in methanol (50 ml)
temperatureThe mixture then heated at 50° C. for 1 h
customThe solvents were then evaporated under reduced pressure
customPurification
filtrationwas by trituration with ethyl acetate and filtration

Sources & evidence

ORD record: ord-0ce68225d99a411dbfe29fac8889b329
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969713B2

Reaction notes

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