Hydrogen chloride-ethyl acetate → 5-piperidin-4-yl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester hydrochloride

HRID 513861Notes

Reaction equation

HRID 513861 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([S:28]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)(=[O:30])=[O:29])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH:15]1[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[ClH:38].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:38].[CH2:1]([O:3][C:4]([C:6]1[N:7]([S:28]([C:31]2[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=2)(=[O:29])=[O:30])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 680052205-(1-tert-butoxycarbonyl-piperidin-4-yl)-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 680052465-piperidin-4-yl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-(1-tert-Butoxycarbonyl-piperidin-4-yl)-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (362 mg, 0.687 mmol) was dissolved in a mixture solution of ethyl acetate (4 ml) and 4 M hydrochloric acid/ethyl acetate (8 ml). This was stirred at room temperature under a nitrogen atmosphere for 1.5 hours. The reaction mixture was concentrated under reduced pressure. Thus, 5-piperidin-4-yl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester hydrochloride was obtained as a colorless amorphous material (332 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b8cb369c3223406492b6ebc0aaadd417
Source dataset
uspto-grants-2015_08
Patent number
US09102692B2

Reaction notes

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