Hydrochloric Acid → HCID 22250306, compound

HRID 733040Notes

Reaction equation

HRID 733040 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:33]>O1CCOCC1>[ClH:33].[C:27]1([S:24]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]([CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:16]=2)(=[O:25])=[O:26])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22250310HCID 22250310, compound

Product 1

HCID 22250306HCID 22250306, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A stirred solution of 4-[3-(phenylsulfonyl)-1H-indol-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 1.10 mmol) in dioxane is treated with 4N HCl in dioxane (4.5 mL, 18 mmol), stirred for 5 h at ambient temperature and concentrated in vacuo. Crystallization of the resultant solid residue from ethanol:ether affords the title compound as a white solid, 351 mg (82% yield), mp>250° C., identified by HNMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customCrystallization of the resultant solid residue from ethanol

Sources & evidence

ORD record
ord-74163e5b04394da6b3437fb01795ffc5
Source dataset
uspto-grants-2009_09
Patent number
US07589108B2

Reaction notes

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