HCID 70073905, compound → 2-[2-[3-Hydroxy-4-[((3S)-3-pyrrolidinyl)oxy]phenyl]ethyl]-5-benzofurancarboxamidine Dihydrochloride

HRID 54011Notes

Reaction equation

HRID 54011 reaction equation
[ClH:1].C([N:5]1[CH2:9][CH2:8][C@H:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]3[O:20][C:21]4[CH:27]=[CH:26][C:25]([C:28]([NH2:30])=[NH:29])=[CH:24][C:22]=4[CH:23]=3)=[CH:13][C:12]=2[OH:31])[CH2:6]1)(=O)C>Cl>[ClH:1].[ClH:1].[OH:31][C:12]1[CH:13]=[C:14]([CH2:17][CH2:18][C:19]2[O:20][C:21]3[CH:27]=[CH:26][C:25]([C:28]([NH2:30])=[NH:29])=[CH:24][C:22]=3[CH:23]=2)[CH:15]=[CH:16][C:11]=1[O:10][C@H:7]1[CH2:8][CH2:9][NH:5][CH2:6]1

Participants

3

Reactant 1

HCID 70073905HCID 70073905, compound

Product 1

HCID 700749432-[2-[3-Hydroxy-4-[((3S)-3-pyrrolidinyl)oxy]phenyl]ethyl]-5-benzofurancarboxamidine DihydrochlorideYield 64.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1.0 g of 2-[2-[4-[((3S)-1-acetyl-3-pyrrolidinyl)oxy]-3-hydroxyphenyl]ethyl]-5-benzofurancarboxamidine hydrochloride was dissolved in 30 ml of 6N hydrochloric acid, and the solution was refluxed under heating for 4 hours. After distilling off the solvent, the resulting residue was subjected to column chromatography using a column packed with a highly porous polymer type synthetic adsorbent (styrene-divinylbenzene polymer: Diaion HP-20) and using a water/acetonitrile mixture as an elution solvent. In this way, 320 mg of the title compound was obtained in a solid form.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heating for 4 hours
  3. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-a894ef3dd350406dbadfe835d864eee8
Source dataset
uspto-grants-1997_04
Patent number
US05620991

Reaction notes

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