合成路线:Compound can be prepared in several different ways:1) The reduction of 2-bromomethyl-4'-chlorobenzophenone (I) with NaBH4 in methanol gives 2-bromomethyl-4'-chlorobenzhydrol (II),which is then treated with methylamine in methanol.2) The reduction of 2-cyano-4'-chlorobenzophenone (III) with LiAlH4 in THF gives 2-aminomethyl-4'-chlorobenzhydrol (IV),which is acylated with p-toluenesulfonyl chloride in pyridine and methylated with methyl iodide and NaOH in ethanol to give 2-(N-methyl-N-tosylaminomethyl)-4'-chlorobenzhydrol (V).Finally,this compound is hydrolyzed with H2SO4 water at 180 C.3) The reaction of 3-(4-chlorophenyl)phthalide (VI) with methylamine in benzene gives 2-methylaminocarbonyl-4'-chlorobenzhydrol (VII),which is then reduced with LiAlH4 in THF.4) The Grignard reaction of N-methylphthalimide (VIII) with 4-chlorophenylmagnesium bromide (IX) gives 1-(4'-chlorophenyl)-1-hydroxy-2-methyl-3-oxoisoindoline (X),which is reduced with LiAlH4 affording 1-(4'-chlorophenyl)-2-methylisoindoline (XI).The treatment of (XI) with refluxing acetic anhydride yields 2-[(N-methyl-N-acetylamino)methyl]-4'-chloro-O-acetylbenzhydrol (XII),which is finally hydrolyzed with KOH in refluxing ethylene glycol.
参考文献标题:New group of anorexigenic compounds
文献作者:Freter,K.; Gotz,M.; Oliver,J.T.
参考来源:J Med Chem 1970,13(6),1228-30
合成路线:Compound can be prepared in several different ways:1) The reduction of 2-bromomethyl-4'-chlorobenzophenone (I) with NaBH4 in methanol gives 2-bromomethyl-4'-chlorobenzhydrol (II),which is then treated with methylamine in methanol.2) The reduction of 2-cyano-4'-chlorobenzophenone (III) with LiAlH4 in THF gives 2-aminomethyl-4'-chlorobenzhydrol (IV),which is acylated with p-toluenesulfonyl chloride in pyridine and methylated with methyl iodide and NaOH in ethanol to give 2-(N-methyl-N-tosylaminomethyl)-4'-chlorobenzhydrol (V).Finally,this compound is hydrolyzed with H2SO4 water at 180 C.3) The reaction of 3-(4-chlorophenyl)phthalide (VI) with methylamine in benzene gives 2-methylaminocarbonyl-4'-chlorobenzhydrol (VII),which is then reduced with LiAlH4 in THF.4) The Grignard reaction of N-methylphthalimide (VIII) with 4-chlorophenylmagnesium bromide (IX) gives 1-(4'-chlorophenyl)-1-hydroxy-2-methyl-3-oxoisoindoline (X),which is reduced with LiAlH4 affording 1-(4'-chlorophenyl)-2-methylisoindoline (XI).The treatment of (XI) with refluxing acetic anhydride yields 2-[(N-methyl-N-acetylamino)methyl]-4'-chloro-O-acetylbenzhydrol (XII),which is finally hydrolyzed with KOH in refluxing ethylene glycol.
参考文献标题:
文献作者:Freter,K.; et al.
参考来源:CA 982608
合成路线:Compound can be prepared in several different ways:1) The reduction of 2-bromomethyl-4'-chlorobenzophenone (I) with NaBH4 in methanol gives 2-bromomethyl-4'-chlorobenzhydrol (II),which is then treated with methylamine in methanol.2) The reduction of 2-cyano-4'-chlorobenzophenone (III) with LiAlH4 in THF gives 2-aminomethyl-4'-chlorobenzhydrol (IV),which is acylated with p-toluenesulfonyl chloride in pyridine and methylated with methyl iodide and NaOH in ethanol to give 2-(N-methyl-N-tosylaminomethyl)-4'-chlorobenzhydrol (V).Finally,this compound is hydrolyzed with H2SO4 water at 180 C.3) The reaction of 3-(4-chlorophenyl)phthalide (VI) with methylamine in benzene gives 2-methylaminocarbonyl-4'-chlorobenzhydrol (VII),which is then reduced with LiAlH4 in THF.4) The Grignard reaction of N-methylphthalimide (VIII) with 4-chlorophenylmagnesium bromide (IX) gives 1-(4'-chlorophenyl)-1-hydroxy-2-methyl-3-oxoisoindoline (X),which is reduced with LiAlH4 affording 1-(4'-chlorophenyl)-2-methylisoindoline (XI).The treatment of (XI) with refluxing acetic anhydride yields 2-[(N-methyl-N-acetylamino)methyl]-4'-chloro-O-acetylbenzhydrol (XII),which is finally hydrolyzed with KOH in refluxing ethylene glycol.
参考文献标题:
文献作者:Boehringer,C.H.; Sohn
参考来源:US 3635974
合成路线:Compound can be prepared in several different ways:1) The reduction of 2-bromomethyl-4'-chlorobenzophenone (I) with NaBH4 in methanol gives 2-bromomethyl-4'-chlorobenzhydrol (II),which is then treated with methylamine in methanol.2) The reduction of 2-cyano-4'-chlorobenzophenone (III) with LiAlH4 in THF gives 2-aminomethyl-4'-chlorobenzhydrol (IV),which is acylated with p-toluenesulfonyl chloride in pyridine and methylated with methyl iodide and NaOH in ethanol to give 2-(N-methyl-N-tosylaminomethyl)-4'-chlorobenzhydrol (V).Finally,this compound is hydrolyzed with H2SO4 water at 180 C.3) The reaction of 3-(4-chlorophenyl)phthalide (VI) with methylamine in benzene gives 2-methylaminocarbonyl-4'-chlorobenzhydrol (VII),which is then reduced with LiAlH4 in THF.4) The Grignard reaction of N-methylphthalimide (VIII) with 4-chlorophenylmagnesium bromide (IX) gives 1-(4'-chlorophenyl)-1-hydroxy-2-methyl-3-oxoisoindoline (X),which is reduced with LiAlH4 affording 1-(4'-chlorophenyl)-2-methylisoindoline (XI).The treatment of (XI) with refluxing acetic anhydride yields 2-[(N-methyl-N-acetylamino)methyl]-4'-chloro-O-acetylbenzhydrol (XII),which is finally hydrolyzed with KOH in refluxing ethylene glycol.
参考文献标题:
文献作者:Freter,K.; et al.
参考来源:US 3728460
合成路线:Compound can be prepared in several different ways:1) The reduction of 2-bromomethyl-4'-chlorobenzophenone (I) with NaBH4 in methanol gives 2-bromomethyl-4'-chlorobenzhydrol (II),which is then treated with methylamine in methanol.2) The reduction of 2-cyano-4'-chlorobenzophenone (III) with LiAlH4 in THF gives 2-aminomethyl-4'-chlorobenzhydrol (IV),which is acylated with p-toluenesulfonyl chloride in pyridine and methylated with methyl iodide and NaOH in ethanol to give 2-(N-methyl-N-tosylaminomethyl)-4'-chlorobenzhydrol (V).Finally,this compound is hydrolyzed with H2SO4 water at 180 C.3) The reaction of 3-(4-chlorophenyl)phthalide (VI) with methylamine in benzene gives 2-methylaminocarbonyl-4'-chlorobenzhydrol (VII),which is then reduced with LiAlH4 in THF.4) The Grignard reaction of N-methylphthalimide (VIII) with 4-chlorophenylmagnesium bromide (IX) gives 1-(4'-chlorophenyl)-1-hydroxy-2-methyl-3-oxoisoindoline (X),which is reduced with LiAlH4 affording 1-(4'-chlorophenyl)-2-methylisoindoline (XI).The treatment of (XI) with refluxing acetic anhydride yields 2-[(N-methyl-N-acetylamino)methyl]-4'-chloro-O-acetylbenzhydrol (XII),which is finally hydrolyzed with KOH in refluxing ethylene glycol.
参考文献标题:
文献作者:Freter,K.; et al.
参考来源:ZA 6902707
合成路线:Compound can be prepared in several different ways:1) The reduction of 2-bromomethyl-4'-chlorobenzophenone (I) with NaBH4 in methanol gives 2-bromomethyl-4'-chlorobenzhydrol (II),which is then treated with methylamine in methanol.2) The reduction of 2-cyano-4'-chlorobenzophenone (III) with LiAlH4 in THF gives 2-aminomethyl-4'-chlorobenzhydrol (IV),which is acylated with p-toluenesulfonyl chloride in pyridine and methylated with methyl iodide and NaOH in ethanol to give 2-(N-methyl-N-tosylaminomethyl)-4'-chlorobenzhydrol (V).Finally,this compound is hydrolyzed with H2SO4 water at 180 C.3) The reaction of 3-(4-chlorophenyl)phthalide (VI) with methylamine in benzene gives 2-methylaminocarbonyl-4'-chlorobenzhydrol (VII),which is then reduced with LiAlH4 in THF.4) The Grignard reaction of N-methylphthalimide (VIII) with 4-chlorophenylmagnesium bromide (IX) gives 1-(4'-chlorophenyl)-1-hydroxy-2-methyl-3-oxoisoindoline (X),which is reduced with LiAlH4 affording 1-(4'-chlorophenyl)-2-methylisoindoline (XI).The treatment of (XI) with refluxing acetic anhydride yields 2-[(N-methyl-N-acetylamino)methyl]-4'-chloro-O-acetylbenzhydrol (XII),which is finally hydrolyzed with KOH in refluxing ethylene glycol.
参考文献标题:2-(Aminomethyl)benzhydrols
文献作者:Goetz,M.; Freter,K.
参考来源:Can J Chem 1970,48(11),1670-76
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