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

HRID 271231Notes

Reaction equation

HRID 271231 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-b63a10537ccc442aa26f8be2d1a52533
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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