Diisopropylethylamine → (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-{4-[2-(2-methylphenoxy)ethyl]piperazinyl}propan-2-ol

HRID 855570Notes

Reaction equation

HRID 855570 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11].[CH3:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@H:24]([OH:32])[CH2:25][N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:18][C:16]=2[N:17]=1.CCN(C(C)C)C(C)C>CCO>[CH3:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@H:24]([OH:32])[CH2:25][N:26]3[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[CH3:11])[CH2:30][CH2:31]3)=[CH:18][C:16]=2[N:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 16225721-(2-Bromoethoxy)-2-methylbenzeneHCID 29943216(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

Product 1

HCID 11189927(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-{4-[2-(2-methylphenoxy)ethyl]piperazinyl}propan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-1-(2-methylphenoxy)ethane (1.09 g, 5.09 mmol, crude) in EtOH (15 mL) was added (2R)-3-(2-methylbenzothiazol-5-yloxy)-1-piperazinylpropan-2-ol as prepared in Example 3A (250 mg, 0.81 mmol) and DIEA (1.5 mL, 8.6 mmol). The solution was stirred at reflux for 14 hours. Upon cooling, the solution was concentrated to an oil and then purified on an Isco™ (100% EtOAc hold 2 min, 8 min. gradient to 20% MeOH/EtOAc, hold 10 min) to afford (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-{4-[2-(2-methylphenoxy)ethyl]piperazinyl}prop an-2-ol.

Workup

  1. temperatureat reflux for 14 hours
  2. temperatureUpon cooling
  3. concentrationthe solution was concentrated to an oil
  4. custompurified on an Isco™ (100% EtOAc hold 2 min, 8 min. gradient to 20% MeOH/EtOAc, hold 10 min)

Sources & evidence

ORD record
ord-82a48dc664c6442d9aa30f346b811841
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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