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【结 构 式】

【分子编号】21897

【品名】2-(4-benzhydryl-1-piperazinyl)ethyl 3-oxobutanoate

【CA登记号】

【 分 子 式 】C23H28N2O3

【 分 子 量 】380.487

【元素组成】C 72.61% H 7.42% N 7.36% O 12.61%

与该中间体有关的原料药合成路线共 3 条

合成路线1

该中间体在本合成路线中的序号:(V)

1) The reaction of 2-(4-piperazinyl)ethanol (I) with diphenylmethyl bromide (II) by means of K2CO3 in DMF gives 2-[4-(diphenylmethyl)-1-piperazinyl] ethanol (III), which is condensed with diketene (IV) at 80 C to yield 2-[4-(diphenylmethyl)-1-piperazinyl] ethyl acetoacetate (V). The condensation of (V) with 3-nitrobenzaldehyde (VI) gives the intermediate benzylidene derivative (VII), which is finally cyclized with methyl 3-aminocrotonate (VIII) in refluxing isopropanol.

1 Meguro, K.; Kawamatsu, Y.; Aizawa, M.; Nagaoka, A.; Sohda, T.; New 1,4-dihydropyridine derivatives with potent an. Chem Pharm Bull 1985, 33, 9, 3787.
2 Meguro, K.; Nagaoka, A. (Takeda Chemical Industries, Ltd.); Dihydropyridine derivs., their production and use. EP 0138505; JP 1985084269; US 4603135 .
3 Prous, J.; Castaner, J.; CV-4093. Drugs Fut 1988, 13, 3, 207.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 21893 2-(1-piperazinyl)-1-ethanol; 1-piperazineethanol; 1-(2-Hydroxyethyl)piperazine 103-76-4 C6H14N2O 详情 详情
(II) 12079 Bromodiphenylmethane; 1-[Bromo(phenyl)methyl]benzene; Benzhydrylbromide 776-74-9 C13H11Br 详情 详情
(III) 12674 2-(4-Benzhydryl-1-piperazinyl)-1-ethanol C19H24N2O 详情 详情
(IV) 21896 4-methyl-2H-oxet-2-one C4H4O2 详情 详情
(V) 21897 2-(4-benzhydryl-1-piperazinyl)ethyl 3-oxobutanoate C23H28N2O3 详情 详情
(VI) 12646 3-Nitrobenzaldehyde 99-61-6 C7H5NO3 详情 详情
(VII) 21899 2-(4-benzhydryl-1-piperazinyl)ethyl (Z)-2-acetyl-3-(3-nitrophenyl)-2-propenoate C30H31N3O5 详情 详情
(VIII) 11372 Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate C5H9NO2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

2) The reaction of 2-(4-piperazinyl)ethanol (I) with diphenylmethyl bromide (II) by means of K2CO3 in DMF gives 2-[4-(diphenylmethyl)-1-piperazinyl] ethanol (III), which is condensed with diketene (IV) at 80 C to yield 2-[4-(diphenylmethyl)-1-piperazinyl] ethyl acetoacetate (V). The reaction of acetoacetate (V) with NH3 in ethanol gives the corresponding aminocrotonate (IX), which is then cyclized with methyl (3-nitrobenzylidene)acetoacetate (VI) [prepared from methyl acetoacetate (X) and 3-nitrobenzaldehyde (VI)] in refluxing isopropanol.

1 Meguro, K.; Kawamatsu, Y.; Aizawa, M.; Nagaoka, A.; Sohda, T.; New 1,4-dihydropyridine derivatives with potent an. Chem Pharm Bull 1985, 33, 9, 3787.
2 Meguro, K.; Nagaoka, A. (Takeda Chemical Industries, Ltd.); Dihydropyridine derivs., their production and use. EP 0138505; JP 1985084269; US 4603135 .
3 Prous, J.; Castaner, J.; CV-4093. Drugs Fut 1988, 13, 3, 207.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 21893 2-(1-piperazinyl)-1-ethanol; 1-piperazineethanol; 1-(2-Hydroxyethyl)piperazine 103-76-4 C6H14N2O 详情 详情
(II) 12079 Bromodiphenylmethane; 1-[Bromo(phenyl)methyl]benzene; Benzhydrylbromide 776-74-9 C13H11Br 详情 详情
(III) 12674 2-(4-Benzhydryl-1-piperazinyl)-1-ethanol C19H24N2O 详情 详情
(IV) 21896 4-methyl-2H-oxet-2-one C4H4O2 详情 详情
(V) 21897 2-(4-benzhydryl-1-piperazinyl)ethyl 3-oxobutanoate C23H28N2O3 详情 详情
(VI) 12646 3-Nitrobenzaldehyde 99-61-6 C7H5NO3 详情 详情
(IX) 21900 2-(4-benzhydryl-1-piperazinyl)ethyl (E)-3-amino-2-butenoate C23H29N3O2 详情 详情
(X) 11791 methyl 3-oxobutanoate; Methyl acetoacetate 105-45-3 C5H8O3 详情 详情
(XI) 12276 methyl (Z)-2-acetyl-3-(3-nitrophenyl)-2-propenoate C12H11NO5 详情 详情

合成路线3

该中间体在本合成路线中的序号:(V)

3) By cyclization of acetoacetate (V) with aldehyde (VI) and methyl 3-aminocrotonate (VIII) in refluxing isopropanol.

1 Meguro, K.; Kawamatsu, Y.; Aizawa, M.; Nagaoka, A.; Sohda, T.; New 1,4-dihydropyridine derivatives with potent an. Chem Pharm Bull 1985, 33, 9, 3787.
2 Meguro, K.; Nagaoka, A. (Takeda Chemical Industries, Ltd.); Dihydropyridine derivs., their production and use. EP 0138505; JP 1985084269; US 4603135 .
3 Prous, J.; Castaner, J.; CV-4093. Drugs Fut 1988, 13, 3, 207.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 21897 2-(4-benzhydryl-1-piperazinyl)ethyl 3-oxobutanoate C23H28N2O3 详情 详情
(VI) 12646 3-Nitrobenzaldehyde 99-61-6 C7H5NO3 详情 详情
(VIII) 11372 Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate C5H9NO2 详情 详情
Extended Information