Reaction #3714

ord-25abf8f48bd44a67ad9fc5f31b8887db

Reaction equation

CN(C)CC1CCC(C(F)(F)F)CC1=O
(2RS,5RS)-2-dimethylaminomethyl-5-trifluoromethyl-cyclohexanone
O=C1CCCC(C(F)(F)F)C1
3-trifluoromethyl-cyclohexanone
CN(C)C(Cl)Cl
dimethylaminomethylene chloride
→
CN(C)CC1CCC(C(F)(F)F)CC1(O)c1cccc(O)c1.Cl
( 27 )
CN(C)CC1CCC(C(F)(F)F)CC1(O)c1cccc(O)c1.Cl
(1RS,2RS ,5RS)-3-(2-dimethylaminomethyl-1-hydroxy-5-trifluoromethyl-cyclohexyl)-phenol hydrochloride

Reactants

CN(C)CC1CCC(C(F)(F)F)CC1=O
(2RS,5RS)-2-dimethylaminomethyl-5-trifluoromethyl-cyclohexanone
O=C1CCCC(C(F)(F)F)C1
3-trifluoromethyl-cyclohexanone
CN(C)C(Cl)Cl
dimethylaminomethylene chloride

Reagents

None

Solvents

CC#N
acetonitrile

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe 5-epimer (27) of compound (25) was prepared, under the conditions

Procedure

The 5-epimer (27) of compound (25) was prepared, under the conditions given in Example 27, from (2RS,5RS)-2-dimethylaminomethyl-5-trifluoromethyl-cyclohexanone, prepared from 3-trifluoromethyl-cyclohexanone and dimethylaminomethylene chloride in acetonitrile. (27) was obtained in a yield of 27% theoretical and had a melting point of 221°-223° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05733936uspto-grants-1998_03