Réaction #95966

Équation de réaction

p-trifluoromethylbenzoyl chloride

ketal

3,4-Dichloro-N-[(8-(dimethylamino)-1,4-dioxaspiro[4.5]dec-8-yl)methyl]benzamide

triethylamine

→

α,α,α-trifluoro-N-[[8-(dimethylamino)-1,4-dioxaspiro[4.5]dec-8-yl]methyl]-p-toluamide

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Autrewas placed in a refrigerator overnight
2. 2
   AutreUpon removal from the refrigerator
3. 3
   Autrethe bulk of the solvent was removed on a rotary evaporator
4. 4
   ExtractionThe separated aqueous layer was extracted with diethyl ether
5. 5
   Autredried
6. 6
   Autreto yield the crude
7. 7
   AutreRecrystallization
8. 8
   workup.ADDITIONfrom a mixture of methylene chloride and Skellysolve® B
9. 9
   Autregave product

Mode opératoire

A solution of 1.0 g (0.00465 mole) of the ketal from Example 1, part A and 0.47 g (0.65 ml) of triethylamine in 15 ml of THF was cooled in an ice bath. To this cooled solution there was added a solution of 0.97 g (0.00465 mole) of p-trifluoromethylbenzoyl chloride in 10 ml of THF over 10 minutes while stirring. The mixture was placed in a refrigerator overnight. Upon removal from the refrigerator, the bulk of the solvent was removed on a rotary evaporator. The residue was taken up in diethyl ether and aqueous sodium bicarbonate solution. The separated aqueous layer was extracted with diethyl ether. The diethyl ether liquid fractions were pooled and dried to yield the crude, named product, 2.07 g, m.p. 128°-130° C. Recrystallization from a mixture of methylene chloride and Skellysolve® B gave product weighing 1.56 g, m.p. 129°-130.5° C. The elemental analysis was as follows:

Source