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

HRID 1271917Notes

Reaction equation

HRID 1271917 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][CH: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 219116911-(2-Methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-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 1-(2-methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-ol as an oil (1.9 g. 6.2 mmol).

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-87d2d410352f484d8b7cc54f060c1947
Source dataset
uspto-grants-2007_04
Patent number
US07208496B2

Reaction notes

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