Trifluoroacetic acid methylene chloride → 1-(2-Methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-ol

HRID 585064

Reaction equation

HRID 585064 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.FC(F)(F)C(O)=O.C(Cl)Cl>CC(C)=O.C(=O)([O-])[O-].[K+].[K+]>[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

5

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 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 180AcetoneSolventHCID 11430Potassium CarbonateSolvent

Procedure

A solution of 4-[2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]-piperazine-1-carboxylic acid tert-butyl ester, a compound of formula (5) (2.0 g, 4.9 mmol), and 25% trifluoroacetic acid/methylene chloride (20 ml) was allowed to stir at room temperature overnight. The solvent was evaporated (in vacuo) to yield an oil. The oil was diluted with acetone (20 ml) and solid potassium carbonate was added until the foaming stopped. The resulting mixture was allowed to stir overnight. The solution was filtered through Celite 512, and the filtrate was evaporated (in vacuo), to yield an oil. The oil was placed under high vacuum overnight, to yield 1-(2-methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-ol, as a clear viscous oil (3.4 g. 6.3 mmol).

Workup

  1. customThe solvent was evaporated (in vacuo)
  2. customto yield an oil
  3. additionwas added until the foaming
  4. stirringto stir overnight
  5. filtrationThe solution was filtered through Celite 512
  6. customthe filtrate was evaporated (in vacuo)
  7. customto yield an oil
  8. customwas placed under high vacuum overnight

Sources & evidence

ORD record
ord-d07b9fcd9cd9436785e486ee7507f440
Source dataset
uspto-grants-2005_08
Patent number
US06930111B2

Linked notes

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