p-Toluenesulfonic acid → HCID 56949077, compound

HRID 2404407Notes

Reaction equation

HRID 2404407 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.[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 660484-Piperidinol, 1-methyl-HCID 257798Benzothiazol-2-yl-phenyl-methanolHCID 5360545Sodium

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 poored into water, alcalinised with 1N sodium hydroxyde 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-9ffdb2db77df4ac093c22572d7e48905
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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