Reaction #63613

Reaction equation

N-(5-fluoro-2-methylphenyl)tetrahydro-3,3-dimethyl-3H-oxazolo[3,4-a]pyrazine-7(8H)-acetamide

hydrochloric acid

sodium carbonate

→

N-(5-fluoro-2-methylphenyl)-3-(hydroxymethyl)-1-piperazineacetamide

Yield 59.4%

Conditions

Workup

1. 1
   Temperaturerefluxed for 2 hours
2. 2
   ExtractionThe product was extracted with trichloromethane
3. 3
   WashThe extract was washed with water
4. 4
   Otherdried
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe residue was purified by column-chromatography over silica gel using
8. 8
   workup.ADDITIONa mixture of trichloromethane and methanol
9. 9
   OtherThe pure fractions were collected
10. 10
    Otherthe eluent was evaporated
11. 11
    OtherThe residue was triturated in 2,2'-oxybispropane
12. 12
    FiltrationThe product was filtered off
13. 13
    Otherdried

Procedure

A mixture of 8.5 parts of N-(5-fluoro-2-methylphenyl)tetrahydro-3,3-dimethyl-3H-oxazolo[3,4-a]pyrazine-7(8H)-acetamide and 105.6 parts of hydrochloric acid solution 0.5N was stirred and refluxed for 2 hours. The reaction mixture was cooled to room temperature. The whole was alkalized with sodium carbonate and salted out. The product was extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia (85:15 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was triturated in 2,2'-oxybispropane. The product was filtered off and dried, yielding 4.4 parts (59.4%) of N-(5-fluoro-2-methylphenyl)-3-(hydroxymethyl)-1-piperazineacetamide; mp. 127.7° C. (intermediate 145).

Source