Hydrochloric Acid → 2-(4-Ethanesulfonyl-phenyl)-3-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-benzo[b]thiophen-6-ol hydrochloride

HRID 748958Notes

Reaction equation

HRID 748958 reaction equation
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:16][C:15]3[CH:17]=[C:18]([OH:21])[CH:19]=[CH:20][C:14]=3[C:13]=2[O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:25][CH:24]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].[ClH:38]>ClCCl.CO.C(OCC)C>[ClH:38].[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:16][C:15]3[CH:17]=[C:18]([OH:21])[CH:19]=[CH:20][C:14]=3[C:13]=2[O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:25][CH:24]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 444274052-(4-(Ethylsulfonyl)phenyl)-3-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)benzo[b]thiophen-6-ol

Product 1

HCID 690738102-(4-Ethanesulfonyl-phenyl)-3-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-benzo[b]thiophen-6-ol hydrochlorideYield 71%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve the compound of Example 88 (300 mg, 0.56 mmol) in dichloromethane (10 mL) and methanol (0.5 mL). Add 2M HCl in diethyl ether (0.4 mL) and stir for 10 minutes. Concentrate in vacuo and dry the solids in a vacuum oven at 50° C. overnight to give 224 mg of the title compound (71%): mass spectrum (ion spray): m/z=538 (M+H).

Workup

  1. concentrationConcentrate in vacuo
  2. customdry the solids in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-91969cd9c3b448ab91d8ff660693a9c1
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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