Triethylamine → Tert-butyl 4-(6-chloropyridin-3-ylsulfonyl)piperazine-1-carboxylate

HRID 79215Notes

Reaction equation

HRID 79215 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:21][C:22]1[N:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.CO.C(Cl)Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:21][C:22]1[N:27]=[CH:26][C:25]([S:28]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 21226129Dichloromethane methanol

Product 1

HCID 11739940Tert-butyl 4-(6-chloropyridin-3-ylsulfonyl)piperazine-1-carboxylateYield 84.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred ice-cooled solution of tert-butyl 1-piperazinecarboxylate (0.88 g, 4.7 mmol), triethylamine (1.3 mL, 9.4 mmol), and 4-dimethylaminopyridine (0.0058 g, 0.047 mmol) in DCM (10 mL) was added 6-chloropyridine-3-sulfonyl chloride (1.0 g, 4.7 mmol) in one portion. The resulting mixture was stirred at 0° C. and gradually warmed up to ambient temperature for 1.5 h. Upon workup, the mixture was directly subjected to combi-flash column chromatography (methanol/DCM) to give compound 360 (1.44 g, 84% yield) as a white solid.

Workup

  1. temperaturegradually warmed up to ambient temperature for 1.5 h

Sources & evidence

ORD record
ord-d8ee2b73ecaa4d95870b1838d9deaa5e
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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