Cyclohexanone → p-Toluenesulfonic acid

HRID 466256Notes

Reaction equation

HRID 466256 reaction equation
NC1C=CC=CC=1C#N.O.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([OH:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1.C1(=O)CCCCC1>>[C:11]1([CH3:21])[CH:12]=[CH:13][C:14]([S:17]([OH:20])(=[O:18])=[O:19])=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 7967CyclohexanoneHCID 729132-AminobenzonitrileHCID 521998p-Toluenesulfonic acid monohydrate2×

Product 1

HCID 6101p-Toluenesulfonic acid

Procedure

A solution of 2-aminobenzonitrile in xylenes with 0.02-0.05 equiv of p-toluenesulfonic acid monohydrate is heated to reflux with stirring. At reflux, cyclohexanone in xylenes is added. The mixture is refluxed for 8 to 12 hours, cooled and another 1.0-1.5 equiv of p-toluenesulfonic acid monohydrate is added. The mixture is heated to reflux for 3 to 7 hours. The product, as a p-toluenesulfonic acid salt, is isolated by filtration. Basification of this product with aqueous sodium hydroxide and extraction with dichloromethane provide the desired product, tacrine, as a free base.

Workup

  1. temperatureto reflux
  2. temperatureAt reflux
  3. temperatureThe mixture is refluxed for 8 to 12 hours
  4. temperaturecooled
  5. temperatureThe mixture is heated
  6. temperatureto reflux for 3 to 7 hours

Sources & evidence

ORD record
ord-b37260013dd74822be88648782c6d133
Source dataset
uspto-grants-1992_10
Patent number
US05155226

Reaction notes

Loading…