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

HRID 855572Notes

Reaction equation

HRID 855572 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH2:10]2.[CH3:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C@H:28]([OH:36])[CH2:29][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[CH:22][C:20]=2[N:21]=1.CCN(C(C)C)C(C)C>CCO>[CH2:12]1[C:13]2[C:9](=[CH:8][C:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:33]3[CH2:34][CH2:35][N:30]([CH2:29][C@@H:28]([OH:36])[CH2:27][O:26][C:23]4[CH:24]=[CH:25][C:19]5[S:18][C:17]([CH3:16])=[N:21][C:20]=5[CH:22]=4)[CH2:31][CH2:32]3)=[CH:15][CH:14]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 130589654-Bromo-1-indan-5-yloxybutaneHCID 29943216(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

Product 1

HCID 11409334(2R)-3-[4-(4-indan-5-yloxybutyl)piperazinyl]-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-bromo-1-indan-5-yloxybutane (934 mg, 3.46 mmol, crude) in EtOH (10 mL) was treated with (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol as prepared in Example 3A (250 mg, 0.81 mmol) and DIEA (0.57 mL, 3.3 mmol) and refluxed for 14 hours. Upon cooling to RT, the solution was then concentrated under reduced pressure and purified via an Isco™ (100% EtOAc 4 min, 10 min gradient to 25% MeOH/EtOAc, hold 6 min.) to afford (2R)-3-[4-(4-indan-5-yloxybutyl)piperazinyl]-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol.

Workup

  1. temperaturerefluxed for 14 hours
  2. concentrationthe solution was then concentrated under reduced pressure
  3. custompurified via an Isco™ (100% EtOAc 4 min, 10 min gradient to 25% MeOH/EtOAc, hold 6 min.)

Sources & evidence

ORD record
ord-34f688b7ec4e4022bfe2496a8d85fef0
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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