تفاعل #683475

معادلة التفاعل

3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl-N-methylamine hydrochloride

potassium iodide

4-chloro-4'-fluorobutyrophenone

potassium carbonate

→

4'-fluoro-4-[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl-N-methylamino]butyrophenone hydrochloride

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONA mixture of the free base
2. 2
   أخرىprepared from 0.81 g
3. 3
   أخرىThe solvent is removed under vacuum
4. 4
   workup.DISSOLUTIONthe residue dissolved in water
5. 5
   غسيلThe organic layer is washed with water and brine
6. 6
   أخرىevaporated to dryness
7. 7
   workup.ADDITIONA mixture of the residue, 6 ml
8. 8
   أخرىremoved under vacuum
9. 9
   أخرىis collected on a filter
10. 10
    غسيلwashed with ether
11. 11
    أخرىrecrystallized from methanol

الإجراء التجريبي

A mixture of the free base prepared from 0.81 g. of 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl-N-methylamine hydrochloride [I(c)] (obtained as in Example 14C), 0.63 g. of potassium iodide, 0.96 g. of potassium carbonate and 0.87 g. of the 2,2-dimethyl-1,3-propanediol ketal of 4-chloro-4'-fluorobutyrophenone in 15 ml. of dimethylformamide is heated together in an oil bath at about 90° C. for about 20 hours. The solvent is removed under vacuum and the residue dissolved in water and benzene. The organic layer is washed with water and brine and evaporated to dryness. A mixture of the residue, 6 ml. of 2.5 N hydrochloric acid and 12 ml. of methanol is stirred at room temperature for about 1.5 hours and most of the methanol removed under vacuum. The residual suspended solid is collected on a filter, washed with ether and recrystallized from methanol: ethyl acetate to give 4'-fluoro-4-[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl-N-methylamino]butyrophenone hydrochloride [I(c)].

المصدر