Diisopropylethylamine → HCID 68551859, compound

HRID 1868011Notes

Reaction equation

HRID 1868011 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]>ClCCl>[C:23]([C:27]1[CH:32]=[CH:31][C:30]([S:33]([N:11]2[CH2:10][CH2:9][N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[CH2:13][CH2:12]2)(=[O:35])=[O:34])=[CH:29][CH:28]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 114129441-(3-Chloropyridin-2-yl)piperazine

Product 1

HCID 68551859HCID 68551859, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(3-chloropyridin-2-yl)piperazine (316 mg, 1.6 mmol) in anhydrous dichloromethane (5 mL) was added diisopropylethylamine (0.975 mL, 5.6 mmol) then 4-tert-butylbenzene-1-sulfonyl chloride (372.4 mg, 1.6 mmol). The mixture was stirred at room temperature for 1.5 hour. Reaction was complete as determined by TLC. The reaction mixture was purified with flash column chromatography to yield 1-[(4-tert-butylphenyl)sulfonyl]-4-(3-chloropyridin-2-yl)piperazine in 59.3% yield (374 mg) as white solid.

Workup

  1. customReaction
  2. customThe reaction mixture was purified with flash column chromatography

Sources & evidence

ORD record
ord-6df2d929aeb0422f91775552ab973d03
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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