tert-Butyl piperazine-1-carboxylate → (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

HRID 1827877Notes

Reaction equation

HRID 1827877 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@H:13]([OH:16])[CH2:14]C)=[CH:7][C:5]=2[N:6]=1.[N:17]1(C(OC(C)(C)C)=O)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.FC(F)(F)C(O)=O.C(Cl)Cl>CC(C)=O.C(=O)([O-])[O-].[K+].[K+]>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@H:13]([OH:16])[CH2:14][N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 69600520HCID 69600520, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 11430Potassium CarbonateSolvent

Procedure

A solution of (2R)-1-(2-methylbenzothiazol-5-yloxy)butan-2-ol, tert butyl piperazinecarboxylate, 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 (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-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-e176715abf4545b294689f75fd8fe195
Source dataset
uspto-grants-2006_06
Patent number
US07056924B2

Reaction notes

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