Reaction #1758

ord-cf6dff211f2249548afbc224153b66a4

Reaction equation

CN(C)Cc1ccc([C@H]2CC[C@H](OC(=O)Cc3ccc(Cl)cc3)CC2)cc1
trans-O-(4-chlorophenylacetyl)-4-(4-dimethylaminomethylphenyl)-cyclohexanol
Cl
hydrogen chloride
→
CN(C)Cc1ccc([C@H]2CC[C@H](OC(=O)Cc3ccc(Cl)cc3)CC2)cc1.Cl
trans-O-(4-Chlorophenylacetyl)-4-(4-dimethylaminomethylphenyl)-cyclohexanol-hydrochloride

Reactants

CN(C)Cc1ccc([C@H]2CC[C@H](OC(=O)Cc3ccc(Cl)cc3)CC2)cc1
trans-O-(4-chlorophenylacetyl)-4-(4-dimethylaminomethylphenyl)-cyclohexanol
Cl
hydrogen chloride

Reagents

None

Solvents

CC(C)O
isopropanol
CCOCC
diethyl ether

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otheris combined at ambient temperature
  2. 2
    workup.ADDITIONadded dropwise
  3. 3
    OtherThe precipitate formed
  4. 4
    Filtrationsuction filtered
  5. 5
    Washwashed repeatedly with diethyl ether
  6. 6
    Otherdried
  7. 7
    OtherWhite crystals are obtained

Procedure

A solution of 0.39 g (0.001 mol) of trans-O-(4-chlorophenylacetyl)-4-(4-dimethylaminomethylphenyl)-cyclohexanol in 10 ml of diethyl ether is combined at ambient temperature, with stirring, with a 1.5 times equimolar amount of hydrogen chloride in isopropanol added dropwise. The precipitate formed is left for 1 hour at ambient temperature, suction filtered, washed repeatedly with diethyl ether and dried. White crystals are obtained, melting point 231°-233° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726205uspto-grants-1998_03