新产品编号:1500245

合成路线:Diazotization of 4-tert-butylaniline (I) with NaNO2 and HCl,followed by reduction of the resulting diazonium salt with SnCl2 provided hydrazine (II).Fisher indolization with 4-chlorobutyraldehyde (IV),(obtained by hydrogenation of acid chloride (III)),then afforded tryptamine (V).In an alternative procedure,4-phthalimidobutyraldehyde diethyl acetal (VIII) was prepared by treatment of amine (VI) with N-carbethoxyphthalimide (VII).Fisher reaction of (VII) with hydrazine (II) produced the (phthalimidoethyl)indole (IX),which was deprotected with hydrazine to furnish the corresponding tryptamine (V).Subsequent condensation of (V) with di-tert-butyl dicarbonate gave carbamate (X).This was finally reduced by means of LiAlH4 providing the target N-methyl tryptamine.

合成路线:Diazotization of 4-tert-butylaniline (I) with NaNO2 and HCl,followed by reduction of the resulting diazonium salt with SnCl2 provided hydrazine (II).Fisher indolization with 4-chlorobutyraldehyde (IV),(obtained by hydrogenation of acid chloride (III)),then afforded the target tryptamine.In an alternative procedure,4-phthalimidobutyraldehyde diethyl acetal (VII) was prepared by treatment of amine (V) with N-carbethoxyphthalimide (VI).Fisher reaction of (VII) with hydrazine (II) produced the (phthalimidoethyl)indole (VIII),which was deprotected with hydrazine to furnish the corresponding tryptamine.

合成路线:Diazotization of 4-tert-butylaniline (I) with NaNO2 and HCl,followed by reduction of the resulting diazonium salt with SnCl2 provided hydrazine (II).Fisher indolization with 4-chlorobutyraldehyde (IV),(obtained by hydrogenation of acid chloride (III)),then afforded tryptamine (V).In an alternative procedure,4-phthalimidobutyraldehyde diethyl acetal (VIII) was prepared by treatment of amine (VI) with N-carbethoxyphthalimide (VII).Fisher reaction of (VII) with hydrazine (II) produced the (phthalimidoethyl)indole (IX),which was deprotected with hydrazine to furnish the corresponding tryptamine (V).Finally,dimethylation of (V) by means of methyl methanesulfonate provided the target N,N-dimethyl tryptamine.

参考文献标题:Intermediates to tetrahydro-beta-carbolines
文献作者:Audia,J.E.; et al.(Eli Lilly and Company)
参考来源:US 5635528


合成路线:Diazotization of 4-tert-butylaniline (I) with NaNO2 and HCl,followed by reduction of the resulting diazonium salt with SnCl2 provided hydrazine (II).Fisher indolization with 4-chlorobutyraldehyde (IV),(obtained by hydrogenation of acid chloride (III)),then afforded tryptamine (V).In an alternative procedure,4-phthalimidobutyraldehyde diethyl acetal (VIII) was prepared by treatment of amine (VI) with N-carbethoxyphthalimide (VII).Fisher reaction of (VII) with hydrazine (II) produced the (phthalimidoethyl)indole (IX),which was deprotected with hydrazine to furnish the corresponding tryptamine (V).Subsequent condensation of (V) with di-tert-butyl dicarbonate gave carbamate (X).This was finally reduced by means of LiAlH4 providing the target N-methyl tryptamine.

合成路线:Diazotization of 4-tert-butylaniline (I) with NaNO2 and HCl,followed by reduction of the resulting diazonium salt with SnCl2 provided hydrazine (II).Fisher indolization with 4-chlorobutyraldehyde (IV),(obtained by hydrogenation of acid chloride (III)),then afforded the target tryptamine.In an alternative procedure,4-phthalimidobutyraldehyde diethyl acetal (VII) was prepared by treatment of amine (V) with N-carbethoxyphthalimide (VI).Fisher reaction of (VII) with hydrazine (II) produced the (phthalimidoethyl)indole (VIII),which was deprotected with hydrazine to furnish the corresponding tryptamine.

合成路线:Diazotization of 4-tert-butylaniline (I) with NaNO2 and HCl,followed by reduction of the resulting diazonium salt with SnCl2 provided hydrazine (II).Fisher indolization with 4-chlorobutyraldehyde (IV),(obtained by hydrogenation of acid chloride (III)),then afforded tryptamine (V).In an alternative procedure,4-phthalimidobutyraldehyde diethyl acetal (VIII) was prepared by treatment of amine (VI) with N-carbethoxyphthalimide (VII).Fisher reaction of (VII) with hydrazine (II) produced the (phthalimidoethyl)indole (IX),which was deprotected with hydrazine to furnish the corresponding tryptamine (V).Finally,dimethylation of (V) by means of methyl methanesulfonate provided the target N,N-dimethyl tryptamine.
参考文献标题:N-Methyl-5-tert-butyltryptamine: A novel,highly potent 5-HT1D receptor agonist
文献作者:Xu,Y.-C.; Schaus,J.M.; Walker,C.; Krushinski,J.; Adhamm,N.; Zgombick,J.M.; Liang,S.X.; Kohlman,D.T.; Audia,J.E.
参考来源:J Med Chem 1999,42(3),526