4-[2-Hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]-piperazine-1-carboxylic acid tert-butyl ester → (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

HRID 271224

Reaction equation

HRID 271224 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([OH:28])[CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]3[S:25][C:24]([CH3:26])=[N:23][C:22]=3[CH:27]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[CH3:26][C:24]1[S:25][C:21]2[CH:20]=[CH:19][C:18]([O:17][CH2:16][C@H:15]([OH:28])[CH2:14][N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:27][C:22]=2[N:23]=1

Participants

4

Reactant 1

HCID 219355284-[2-Hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 29943216(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-[2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]-piperazine-1-carboxylic acid tert-butyl ester (2.9 g, 7.1 mmol), a compound of formula (5), was dissolved in a 4N solution of HCl in dioxane (20 ml) and allowed to stir at room temperature for 4 hours. The solvent was evaporated under reduced pressure to yield a white solid. The white solid was dried under high vacuum, and then dissolved in methanol (250 ml). AG 1-X8 resin was added and the mixture shaken. Additional resin was added until a neutral pH was obtained. The resin beads were removed by filtration, and methanol removed from the filtrate under reduced pressure, and the residue placed under high vacuum overnight, to yield (2R)-3-(2-methylbenzothiazol-5-yloxy)-1-piperazinylpropan-2-ol as an oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto yield a white solid
  3. customThe white solid was dried under high vacuum
  4. dissolutiondissolved in methanol (250 ml)
  5. additionAG 1-X8 resin was added
  6. stirringthe mixture shaken
  7. additionAdditional resin was added until a neutral pH
  8. customwas obtained
  9. customThe resin beads were removed by filtration, and methanol
  10. customremoved from the filtrate under reduced pressure
  11. customplaced under high vacuum overnight

Sources & evidence

ORD record
ord-da0dde98791a4e7bbda0176abbb27583
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Linked notes

Loading…