p-Toluenesulfonic acid → HCID 56949077, compound

HRID 572819Notes

Reaction equation

HRID 572819 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:11].O[CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:25][N:22]1[CH2:23][CH2:24][CH:19]([O:11][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 660484-Piperidinol, 1-methyl-HCID 257798Benzothiazol-2-yl-phenyl-methanol

Product 1

HCID 56949077HCID 56949077, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of benzothiazol-2-ylphenylmethanol (0.36 g), 4-hydroxy-1-methylpiperidine (0.17 g) and para-toluenesulfonic acid (0.57 g) in toluene (22 mL) is heated overnight in a Dean-Stark apparatus. The mixture is cooled back to room temperature and poured into water, alcalinised with 1N sodium hydroxide and extracted twice with ethyl acetate. Pooled organic extracts are washed with brine, dried over magnesium sulfate and concentrated. The residue is purified by column chromatography over silica gel (gradient dichloromethane/methanol from 98/2 to 90/10) to give 2-[(1-methylpiperidin-4-yloxy)phenylmethyl]benzothiazole melting at 115° C.

Workup

  1. temperatureis heated overnight in a Dean-Stark apparatus
  2. extractionextracted twice with ethyl acetate
  3. washPooled organic extracts are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography over silica gel (gradient dichloromethane/methanol from 98/2 to 90/10)

Sources & evidence

ORD record
ord-bf9f9759397a40caa1e27df2eb5e7eb2
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

Loading…