تفاعل #2485997

معادلة التفاعل

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

3',4'-Dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ylamine hydrochloride

potassium iodide

4-chloro-4'-fluorobutyrophenone

potassium carbonate

→

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

المردود 39.0%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent is removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue that remains is dissolved in benzene
3. 3
   غسيلThe organic layer is washed with water and brine
4. 4
   أخرىevaporated to dryness
5. 5
   workup.ADDITIONA mixture of the residue and 10 ml
6. 6
   أخرىThe methanol is then removed under vacuum
7. 7
   أخرىthe solid collected on a filter
8. 8
   أخرىThis material is recrystallized twice from methylene chloride
9. 9
   أخرىethyl acetate to give 1.07 g

الإجراء التجريبي

The free base from 1.65 g. (0.0066 M) of 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ylamine hydrochloride [I(c)] (prepared in Example 10C), 1.34 g. of potassium iodide, 2.06 g. of potassium carbonate and 1.9 g. of the 2,2-dimethyl-1,3-propanediol ketal of 4-chloro-4'-fluorobutyrophenone in 35 ml. of dimethylformamide are heated in an oil bath at about 90° C. for about 18 hours. The solvent is removed under vacuum and the residue that remains is dissolved in benzene and water. The organic layer is washed with water and brine and evaporated to dryness. A mixture of the residue and 10 ml. of 2.5 N hydrochloric acid in 20 ml. of methanol is stirred at room temperature for about 4 hours. The methanol is then removed under vacuum and the solid collected on a filter. This material is recrystallized twice from methylene chloride: ethyl acetate to give 1.07 g. (39% yield) of 4'-fluoro-4-[[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl]amino]butyrophenone hydrochloride [I(c)], having a melting point of 182° to 184° C.

المصدر