Preparation of imidazo{8 2,1-a{9 isoindoles

Claim 2

R, R1 AND R2 ARE SUCH THAT THERE IS NEVER A TRIFLUOROMETHYL RADICAL ON EACH OF TWO ADJACENT CARBON ATOMS, AND

Claim 3

A PROCESS FOR PREPARING A COMPOUND OF THE FORMULA

Claim 4

A PROCESS FOR PREPARING A COMPOUND OF THE FORMULA

Claim 5

WHEN R OR R2 IS TRIFLUOROMETHYL, R1 IS HYDROGEN, CHLORO OR FLUORO, EACH OF R3, R4 AND R5 IS INDEPENDENTLY, HYDROGEN, CHLORO OF FLUORO, AND R6 IS HYDRGONE OR FLUORO, PROVIDED FURTHER THAT NOT MORE THAN TWO OF R3,R4,R5 AND R6 ARE OTHER THAN HYDROGEN AND THAT NOT MORE THAN THREE OF R,R1, R2,R3,R4,R5 AND R6 ARE OTHER THAN HYDROGEN,

Claim 6

WHEN R OR R2 IS TRIFLUOROMETHYL, R1 IS HYDROGEN, CHLORO OR FLUORO, EACH OF R3, R4 AND R5 IS INDEPENDENTLY, HYDROGEN, CHLORO OF FLUORO, AND R6 IS HYDRGONE OR FLUORO, PROVIDED FURTHER THAT NOT MORE THAN TWO OF R3,R4,R5 AND R6 ARE OTHER THAN HYDROGEN AND THAT NOT MORE THAN THREE OF R,R1, R2,R3,R4,R5 AND R6 ARE OTHER THAN HYDROGEN,

Claim 7

The process of claim 1 wherein the reduction is effected under a nitrogen atmosphere and at a temperature of from about 45* to 85*C.

Claim 8

when R or R2 is trifluoromethyl, R1 is hydrogen, chloro or fluoro; each of R3, R4 and R5 is independently, hydrogen, chloro of fluoro, and R6 is hydrogen or fluoro, provided further that not more than two of R3, R4, R5 and R6 are other than hydrogen and that not more than three of R, R1, R2, R3, R4, R5 and R6 are other than hydrogen.

Claim 9

when R or R2 is trifluoromethyl, R1 is hydrogen, chloro or fluoro; each of R3, R4 and R5 is independently, hydrogen, chloro of fluoro, and R6 is hydrogen or fluoro, provided further that not more than two of R3, R4, R5 and R6 are other than hydrogen and that not more than three of R, R1, R2, R3, R4, R5 and R6 are other than hydrogen.

Claim 10

A process for preparing 5-(p-chlorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole which comprises reducing 2-( Beta -aminoethyl)-3-(p-chlorophenyl)phthalimidine in inert ether and under inert atmosphere with lithium aluminum hydride at a temperature of from about 45* to about 85*C. for a period of time sufficient to form the desired product.

Claim 11

A process for preparing 5-(p-chlorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole which comprises reducing 2-( Beta -aminoethyl)-3-(p-chlorophenyl)phthalimidine in inert ether and under inert atmosphere with lithium aluminum hydride at a temperature of from about 45* to about 85*C. for a period of time sufficient to form the desired product.

Claim 12

A process for preparing a. 5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, b. 5-(p-fluorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, c. 5-(p-methoxyphenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, d. 5-(3,4-dichlorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, e. 5-(m-chlorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, f. 5-(p-trifluoromethylphenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, g. 5-(p-tolyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, h. 5-(p-ethylphenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, i. 6-chloro-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, j. 5-(m-trifluoromethylphenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, k. 5-(m-fluorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, l. 5-(3,5-dichlorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, m. 7,8-dichloro-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, n. 5-(p-chlorophenyl)-7,8-dichloro-2,3-dihydro-5H-imidazo(2,1-a)isoindole, o. 8-chloro-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, p. 7-chloro-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, or g. 7-fluoro-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, which comprises reducing a. 2-( Beta -aminoethyl)-3-phenylphthalimidine, b. 2-( Beta -aminoethyl)-3-(p-fluorophenyl)phthalimidine, c. 2-( Beta -aminoethyl)-3-(p-methoxyphenyl)-phthalimidine, d. 2-( Beta -aminoethyl)-3-(3,4-dichlorophenyl)phthalimidine, e. 2-( Beta -aminoethyl)-3-(m-chlorophenyl)phthalimidine, f. 2-( Beta -aminoethyl)-3-(p-trifluoromethylphenyl)phthalimidine, g. 2-( Beta -aminoethyl)-3-(p-tolyl)phthalimidine, h. 2-( Beta -aminoethyl)-3-(p-ethylphenyl)phthalimidine, i. 2-( Beta -aminoethyl)-4-chloro-3-phenyl phthalimidine, j. 2-( Beta -aminoethyl)-3-(m-trifluoromethylphenyl)phthalimidine, k. 2-( Beta -aminoethyl)-3-(m-fluorophenyl)phthalimidine, l. 2-( Beta -aminoethyl)-3-(3,5-dichlorophenyl)phthalimidine, m. 2-( Beta -aminoethyl)-5,6-dichloro-3-phenyl phthalimidine, n. 2-( Beta -aminoethyl)-3-(p-chlorophenyl)-5,6-dichlorophthalimidine, o. 2-( Beta -amInoethyl)-6-chloro-3-phenyl phthalimidine, p. 2-( Beta -aminoethyl)-5-chloro-3-phenyl phthalimidine, or q. 2-( Beta -aminoethyl)-5-fluoro-3-phenyl phthalimidine, respectively, in inert ether and under inert atmosphere with lithium aluminum hydride at a temperature of from about 45* to about 85*C., for a period of time sufficient to form the desired corresponding product.

Claim 13

A process for preparing a. 5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, b. 5-(p-fluorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, c. 5-(p-methoxyphenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, d. 5-(3,4-dichlorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, e. 5-(m-chlorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, f. 5-(p-trifluoromethylphenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, g. 5-(p-tolyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, h. 5-(p-ethylphenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, i. 6-chloro-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, j. 5-(m-trifluoromethylphenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, k. 5-(m-fluorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, l. 5-(3,5-dichlorophenyl)-2,3-dihydro-5H-imidazo(2,1-a)isoindole, m. 7,8-dichloro-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, n. 5-(p-chlorophenyl)-7,8-dichloro-2,3-dihydro-5H-imidazo(2,1-a)isoindole, o. 8-chloro-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, p. 7-chloro-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, or g. 7-fluoro-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindole, which comprises reducing a. 2-( Beta -aminoethyl)-3-phenylphthalimidine, b. 2-( Beta -aminoethyl)-3-(p-fluorophenyl)phthalimidine, c. 2-( Beta -aminoethyl)-3-(p-methoxyphenyl)-phthalimidine, d. 2-( Beta -aminoethyl)-3-(3,4-dichlorophenyl)phthalimidine, e. 2-( Beta -aminoethyl)-3-(m-chlorophenyl)phthalimidine, f. 2-( Beta -aminoethyl)-3-(p-trifluoromethylphenyl)phthalimidine, g. 2-( Beta -aminoethyl)-3-(p-tolyl)phthalimidine, h. 2-( Beta -aminoethyl)-3-(p-ethylphenyl)phthalimidine, i. 2-( Beta -aminoethyl)-4-chloro-3-phenyl phthalimidine, j. 2-( Beta -aminoethyl)-3-(m-trifluoromethylphenyl)phthalimidine, k. 2-( Beta -aminoethyl)-3-(m-fluorophenyl)phthalimidine, l. 2-( Beta -aminoethyl)-3-(3,5-dichlorophenyl)phthalimidine, m. 2-( Beta -aminoethyl)-5,6-dichloro-3-phenyl phthalimidine, n. 2-( Beta -aminoethyl)-3-(p-chlorophenyl)-5,6-dichlorophthalimidine, o. 2-( Beta -amInoethyl)-6-chloro-3-phenyl phthalimidine, p. 2-( Beta -aminoethyl)-5-chloro-3-phenyl phthalimidine, or q. 2-( Beta -aminoethyl)-5-fluoro-3-phenyl phthalimidine, respectively, in inert ether and under inert atmosphere with lithium aluminum hydride at a temperature of from about 45* to about 85*C., for a period of time sufficient to form the desired corresponding product.