Hydrochloric Acid → 1-Benzenesulfonyl-3-piperidin-3-yl-1H-indole

HRID 1884832Notes

Reaction equation

HRID 1884832 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CC(C)([O-])C.[K+].Cl>O1CCCC1>[C:23]1([S:29]([N:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([CH:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[CH:15]2)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 69373374Tert-butyl 3-(1h-indol-3-yl)piperidine-1-carboxylate

Product 1

HCID 99025331-Benzenesulfonyl-3-piperidin-3-yl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(1H-indol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (75 mg, 0.25 mmol) and phenylsulfonyl chloride (50 mg, 0.27 mmol) in tetrahydrofuran (THF) at room temperature is treated with potassium tert-butoxide (0.275 mL, 1 M solution in THF, 0.275 mmol), shaken at room temperature for 16 hours, treated with HCl (4 N in dioxane, 0.5 mL), shaken for 2 hours and concentrated in vacuo to give a residue. Purification of the residue by HPLC1 affords the title product, characterized by HPLC and mass spectral analyses [M+H] 341.45, LCMS2 retention time 1.67 min.

Workup

  1. stirringshaken for 2 hours
  2. concentrationconcentrated in vacuo
  3. customto give a residue
  4. customPurification of the residue by HPLC1

Sources & evidence

ORD record
ord-f7d2fdc0a54d42d2ad602cfba44ab499
Source dataset
uspto-grants-2004_07
Patent number
US06767912B2

Reaction notes

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