p-Toluenesulfonic acid monohydrate → 4-[2-(Dimethylamino)thiazol-4-yl]-4-phenylpiperidine p-toluenesulfonate

HRID 1684772Notes

Reaction equation

HRID 1684772 reaction equation
Br.Br[CH2:3][C:4]([C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=O.[CH3:18][N:19]([CH3:23])[C:20]([NH2:22])=[S:21].O.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1>CCO.CC(C)=O>[C:25]1([CH3:35])[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:32])=[O:33])=[CH:29][CH:30]=1.[CH3:18][N:19]([CH3:23])[C:20]1[S:21][CH:3]=[C:4]([C:6]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:22]=1

Participants

6

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 30341921,1-Dimethyl-2-thioureaHCID 227417564-(2-Bromoacetyl)-4-phenylpiperidine hydrobromide

Product 1

HCID 212005544-[2-(Dimethylamino)thiazol-4-yl]-4-phenylpiperidine p-toluenesulfonateYield 76.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 702EthanolSolvent

Procedure

A mixture of 7.26 g of the compound obtained in step B) and 2.08 g of the compound obtained in step A) in 150 ml of EtOH is refluxed for 1 hour 30 minutes. After cooling to RT, the mixture is concentrated under vacuum, the residue is taken up with water, rendered alkaline to pH 10 by the addition of 10% NaOH solution and extracted with DCM, the organic phase is washed with 10% NaOH solution and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The product obtained is dissolved in acetone, a solution of 3.31 g of p-toluenesulfonic acid monohydrate in 10 ml of acetone is added dropwise and the crystalline product formed is wrung to give 6.1 g of the expected product. M.p.=164° C.

Workup

  1. temperatureis refluxed for 1 hour 30 minutes
  2. concentrationthe mixture is concentrated under vacuum
  3. additionby the addition of 10% NaOH solution
  4. extractionextracted with DCM
  5. washthe organic phase is washed with 10% NaOH solution and with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customthe solvent is evaporated off under vacuum
  8. customThe product obtained
  9. customthe crystalline product formed

Sources & evidence

ORD record
ord-d1a9a495eb894966b5f38f506eba0ae6
Source dataset
uspto-grants-1997_06
Patent number
US05641777

Reaction notes

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