Reaction #1810807

ord-6865711830564f9ba16c6da1dc7ac535

Reaction equation

O
H2O
CNC(=S)NC1CCC(N(C)C)CC1
1-(4-dimethylaminocyclohexyl)-3-methyl-thiourea
CI
methyliodide
Cl
HCl
CN=C(N[C@H]1CC[C@H](N(C)C)CC1)SC
1-(trans-4-Dimethylamino-cyclohexyl)-2,3-dimethyl-isothiourea
Cl
hydrochloride

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherFrom the mixture obtained solvent
  2. 2
    Otheris evaporated
  3. 3
    Otherthe evaporation residue obtained
  4. 4
    Otherobtained
  5. 5
    Otherthe mixture obtained
  6. 6
    workup.STIRRINGis stirred at RT
  7. 7
    OtherA precipitate obtained
  8. 8
    Filtrationis filtrated off
  9. 9
    Otherthe filtrate obtained

Procedure

A mixture of 0.50 g of 1-(4-dimethylaminocyclohexyl)-3-methyl-thiourea in 10 ml of MeOH, 1.16 ml of 2M HCl (in MeOH) and 0.36 g of methyliodide is stirred at RT. From the mixture obtained solvent is evaporated and the evaporation residue obtained is treated with H2O. 10 ml of a strong basic ion exchanger in chloride form (Amberlite IRA 400 (Cl)R) are added to the aqueous mixture obtained and the mixture obtained is stirred at RT. A precipitate obtained is filtrated off and the filtrate obtained is lyophilized. 1-(trans-4-Dimethylamino-cyclohexyl)-2,3-dimethyl-isothiourea in the form of a hydrochloride is obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07485632B2uspto-grants-2009_02