Diisopropylethylamine → (2R)-3-[4-(4-cyclopentyloxybutyl)piperazinyl]-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol

HRID 271226Notes

Reaction equation

HRID 271226 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.CCN(C(C)C)C(C)C.[CH3:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH:33]([OH:41])[CH2:34][N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)=[CH:27][C:25]=2[N:26]=1>CCO>[CH:7]1([O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:38]2[CH2:39][CH2:40][N:35]([CH2:34][C@@H:33]([OH:41])[CH2:32][O:31][C:28]3[CH:29]=[CH:30][C:24]4[S:23][C:22]([CH3:21])=[N:26][C:25]=4[CH:27]=3)[CH2:36][CH2:37]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 219116911-(2-Methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-olHCID 21935507(4-Bromobutoxy)cyclopentane

Product 1

HCID 11166773(2R)-3-[4-(4-cyclopentyloxybutyl)piperazinyl]-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (4-bromobutoxy)cyclopentane (400 mg, 1.81 mmol) in EtOH (5 mL) was treated with DIEA (0.64 mL, 3.62 mmol) and 1-(2-methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-ol as prepared in Example 3A (557 mg, 1.81 mmol). The solution was stirred at reflux 15 hours. Upon cooling, the product was concentrated and purified by flash column chromatography (10% MeOH/EtOAc) to yield (2R)-3-[4-(4-cyclopentyloxybutyl)piperazinyl]-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol.

Workup

  1. temperatureat reflux 15 hours
  2. temperatureUpon cooling
  3. concentrationthe product was concentrated
  4. custompurified by flash column chromatography (10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-2bcaf84f35474dc8a95739f602aef254
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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