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【结 构 式】 
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【分子编号】51139 【品名】tert-butyl 4-[(cyclohexylmethyl)amino]butyl([1-[2-(1-naphthyl)acetyl]-4-piperidinyl]methyl)carbamate 【CA登记号】 |
【 分 子 式 】C34H51N3O3 【 分 子 量 】549.79736 【元素组成】C 74.28% H 9.35% N 7.64% O 8.73% |
合成路线1
该中间体在本合成路线中的序号：(XII)The primary amino group of 4-(aminomethyl)piperidine (I) was protected by conversion to the phthalimide (III) upon heating with phthalic anhydride (II). After coupling of piperidine (III) with 1-naphthylacetic acid (IV) to give amide (V), hydrazinolysis of the phthalimido group of (V) liberated the primary amine (VI). Alkylation of (VI) with N-(4-bromobutyl)phthalimide (VII) furnished the secondary amine (VIII), which was further protected with a tert-butoxycarbonyl group to provide (IX). The phthaloyl group of (IX) was then removed by hydrazinolysis, yielding amine (X). This was subjected to reductive alkylation with cyclohexanecarboxaldehyde (XI) in the presence of NaBH4 to afford the cyclohexylmethyl amine (XII). After purification as the di-Boc derivative, acid cleavage of the tert-butyl carbamate groups provided the title compound.
| 【1】 Yoneda, Y.; et al.; Synthesis of diaminobutane derivatives as potent Ca2+-permeable AMPA receptor antagonists. Bioorg Med Chem Lett 2001, 11, 19, 2663. |
| 【2】 Ito, M.; Yoneda, Y.; Kawagoe, K.; Yasukouchi, T.; Kito, F.; Mimura, T.; Kawajiri, S.; Sugimura, M.; Saito, M.; Tatematu, T.; Discovery of diaminobutane derivatives as Ca2+ -permeable AMPA receptor antagonists. Bioorg Med Chem 2002, 10, 5, 1347. |
| 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) | 19349 | 4-piperidinylmethylamine; 4-piperidinylmethanamine; 4-(Aminomethyl)piperidine | 7144-05-0 | C6H14N2 | 详情 | 详情 |
| (II) | 11900 | 2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride | 85-44-9 | C8H4O3 | 详情 | 详情 |
| (III) | 51132 | 2-(4-piperidinylmethyl)-1H-isoindole-1,3(2H)-dione | C14H16N2O2 | 详情 | 详情 | |
| (IV) | 51133 | Planofix; alpha-Naphthylacetic acid; 1-Naphthaleneacetic acid; 1-Naphthylacetic acid; alpha-Naphthaleneacetic acid; Naphthalene-1-acetic acid | 86-87-3 | C12H10O2 | 详情 | 详情 |
| (V) | 51134 | 2-([1-[2-(1-naphthyl)acetyl]-4-piperidinyl]methyl)-1H-isoindole-1,3(2H)-dione | C26H24N2O3 | 详情 | 详情 | |
| (VI) | 51135 | 1-[4-(aminomethyl)-1-piperidinyl]-2-(1-naphthyl)-1-ethanone | C18H22N2O | 详情 | 详情 | |
| (VII) | 17163 | N-(4-Bromobutyl)phthalimide; 2-(4-Bromobutyl)-1H-isoindole-1,3(2H)-dione | 5394-18-3 | C12H12BrNO2 | 详情 | 详情 |
| (VIII) | 51136 | 2-[4-[([1-[2-(1-naphthyl)acetyl]-4-piperidinyl]methyl)amino]butyl]-1H-isoindole-1,3(2H)-dione | C30H33N3O3 | 详情 | 详情 | |
| (IX) | 51137 | tert-butyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl([1-[2-(1-naphthyl)acetyl]-4-piperidinyl]methyl)carbamate | C35H41N3O5 | 详情 | 详情 | |
| (X) | 51138 | tert-butyl 4-aminobutyl([1-[2-(1-naphthyl)acetyl]-4-piperidinyl]methyl)carbamate | C27H39N3O3 | 详情 | 详情 | |
| (XI) | 33694 | cyclohexanecarbaldehyde | 2043-61-0 | C7H12O | 详情 | 详情 |
| (XII) | 51139 | tert-butyl 4-[(cyclohexylmethyl)amino]butyl([1-[2-(1-naphthyl)acetyl]-4-piperidinyl]methyl)carbamate | C34H51N3O3 | 详情 | 详情 |