(2s)-1-(4-Benzo[b]furanoxy)-3-(4-(3-(3-dimethylaminopropyl)-benzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol oxalate hydrate → (2S)-1-(7-Benzo[b]furanoxy)-3-(4-(3-(3-dimethylaminopropyl)-benzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol Oxalate Hemihydrate

HRID 1760622Notes

Reaction equation

HRID 1760622 reaction equation
O.[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4].O1C=CC2C([O:17][CH2:18][C@@H:19]([OH:42])[CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[S:31][C:30]5[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=5[C:28]=4[CH2:36][CH2:37][CH2:38][N:39]([CH3:41])[CH3:40])[CH2:23][CH2:22]3)=CC=CC1=2.[O:43]1[CH2:45][C@H:44]1[CH2:46][O:47][C:48]1[C:53]2[O:54][CH:55]=[CH:56][C:52]=2[CH:51]=[CH:50][CH:49]=1>CO>[OH2:4].[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4].[O:54]1[CH:55]=[CH:56][C:52]2[CH:51]=[CH:50][CH:49]=[C:48]([O:17][CH2:18][C@@H:19]([OH:42])[CH2:20][N:21]3[CH2:22][CH2:23][CH:24]([C:27]4[S:31][C:30]5[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=5[C:28]=4[CH2:36][CH2:37][CH2:38][N:39]([CH3:41])[CH3:40])[CH2:25][CH2:26]3)[C:53]1=2.[O:54]1[CH:55]=[CH:56][C:52]2[CH:51]=[CH:50][CH:49]=[C:48]([O:47][CH2:46][C@@H:44]([OH:43])[CH2:45][N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[S:31][C:30]5[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=5[C:28]=4[CH2:36][CH2:37][CH2:38][N:39]([CH3:41])[CH3:40])[CH2:23][CH2:22]3)[C:53]1=2.[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 20751429(2s)-1-(4-Benzo[b]furanoxy)-3-(4-(3-(3-dimethylaminopropyl)-benzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol oxalate hydrateHCID 86590504(S)-(+)-7-(oxiranylmethoxy)-benzo[b]furan

Product 1

HCID 131724712(2S)-1-(7-Benzo[b]furanoxy)-3-(4-(3-(3-dimethylaminopropyl)-benzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol Oxalate HemihydrateYield 39.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 4-(3-(3-dimethylaminopropyl)benzo[b]thiophen-2-yl)piperidine (0.075 g, 0.248 mmol, prepared in example 15) and (S)-(+)-7-(oxiranylmethoxy)benzo[b]furan (0.047 g, 0.248 mmol) in methanol (3 mL) was heated at reflux for 18 hours and then cooled and evaporated. The residue was purified using silica gel chromatography (dichloromethane/10% methanol/1% ammonium hydroxide in dichloromethane gradient elution) to give the title compound as a yellow oil (0.039 g, 32%). The oxalate was prepared to give the title compound. FDMS m/e=493 (M++1 of free base). C29H36N2O3S.C2H2O4.0.5H2O

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. customevaporated
  4. customThe residue was purified
  5. washsilica gel chromatography (dichloromethane/10% methanol/1% ammonium hydroxide in dichloromethane gradient elution)

Sources & evidence

ORD record
ord-b2581cbbe671495d9962d90a9b1fd892
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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