Potassium Carbonate → 1-(2-Benzothiazolyl)-4-piperidinemethanol

HRID 484060Notes

Reaction equation

HRID 484060 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Cl[C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[S:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:10]1[N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119872-ChlorobenzothiazoleHCID 4207714-Piperidinemethanol

Product 1

HCID 197495981-(2-Benzothiazolyl)-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

30 g of 4-hydroxymethylpiperidine, 44 g of 2-chlorobenzothiazole and 72 g of potassium carbonate are reacted in 600 ml of acetonitrile under reflux overnight. After filtration and evaporation of the solvent, the residue is taken up in 200 ml of ethyl acetate and extracted with 1N hydrochloric acid. The aqueous phase is made alkaline with caustic soda and extracted with dichloromethane. The expected product is obtained by drying and evaporation.

Workup

  1. temperatureunder reflux overnight
  2. filtrationAfter filtration and evaporation of the solvent
  3. extractionextracted with 1N hydrochloric acid
  4. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-dbea2f4798a04c9585a5415e578b8940
Source dataset
uspto-grants-1993_07
Patent number
US05229398

Reaction notes

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