Triethylamine → HCID 86753990, compound

HRID 1419614Notes

Reaction equation

HRID 1419614 reaction equation
Cl.[N:2]1([C:8]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=3)[NH:13][CH:12]=2)=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N([CH2:27][CH3:28])CC)C.[C:29]1(C)[C:30]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:32]=C[CH:34]=1>C(Cl)(Cl)Cl>[C:27]1([CH3:28])[CH:32]=[CH:31][C:30]([S:35]([N:5]2[CH2:6][CH2:7][N:2]([C:8]([CH2:10][C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=4)[NH:13][CH:12]=3)=[O:9])[CH2:3][CH2:4]2)(=[O:37])=[O:36])=[CH:29][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 18800608HCID 18800608, compound

Product 1

HCID 86753990HCID 86753990, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 3-(piperazinecarbonyl)methyl-5-cyanoindole hydrochloride (200 mg, 0.66 mmol) and triethylamine (134 mg, 185 μL) in chloroform was added toluenesulfonylchloride (126 mg, 0.66 mmol). After stirring for 18 h at rt under a nitrogen atmosphere, the reaction was quenched with water, extracted with chloroform, washed with 1N HCl, sat sodium bicarbonate, and brine, dried with sodium sulfate, filtered and concentrated in vacuo to afford 237 mg of product. LRMS (M+H)+ 423.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with chloroform
  3. washwashed with 1N HCl
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9588caa1c0648f6808f10bb4c7c9ae0
Source dataset
uspto-grants-1999_03
Patent number
US05886191

Reaction notes

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