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

HRID 484064Notes

Reaction equation

HRID 484064 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 1 N 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 1 N hydrochloric acid
  4. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-250f6729c0fa49de9efe3da788efbe95
Source dataset
uspto-grants-1993_07
Patent number
US05229399

Reaction notes

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