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【结 构 式】 
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【分子编号】32211 【品名】(1-allyl-2-pyrrolidinyl)methanamine; (1-allyl-2-pyrrolidinyl)methylamine 【CA登记号】66411-51-6 |
【 分 子 式 】C8H16N2 【 分 子 量 】140.22852 【元素组成】C 68.52% H 11.5% N 19.98% |
合成路线1
该中间体在本合成路线中的序号：(II)By reaction of 5-aminosulfonyl-2,3-dimethoxybenzoic acid (I) with 1-allyl-2-aminomethylpyrrolidine (II).
| 【1】 Thominet, M.L.; Perrot, J.J.; N-(1-allyl-2-pyrrolidylmethyl)-2,3-dimethoxy-5-sulfamoylbenzamide and derivatives thereof and method for treating hot flushes associated with natural or surgical menopause. DD 137670; ES 460621; FR 2358892; GB 1539319; JP 53038631; US 4499019 . |
| 【2】 Castaner, J.; Serradell, M.N.; Neuman, M.; Blancafort, P.; Veralipride. Drugs Fut 1981, 6, 1, 46. |
合成路线2
该中间体在本合成路线中的序号：(V)The nitration of methyl 2-methoxy-4-aminobenzoate (I) with nitric acid in acetic acid-acetic anhydride, followed by hydrolysis with methanolic H2SO4 gives methyl 2-methoxy-4-amino-5-nitrobenzoate (II), which is reduced with H2 over Raney-Ni in methanol to yield methyl-2-methoxy-4,5-diaminohenzoate (III). The cyclization of (III) with NaNO2 in aqueous HCl affords methyl 6-methoxybenzotriazole-5-carboxylate (IV), which is finally condensed with 1-allylpyrrolidin-2-ylmethylamine (V) in refluxing toluene.
| 【1】 Leeson, P.A.; Serradell, M.N.; Castaner, J.; Blancafort, P.; Mealy, N.E.; Alizapride. Drugs Fut 1981, 6, 1, 11. |
| 【2】 Bulteau, G.; Acher, J.; Collignon, C.; Monier, J.-C. (Societe d'Etudes Scientifiques et Industrielles de L'Ile de France); N-(1'-allypyrrolidinyl-2'-methyl)-2-methoxy-4,5-azimido benzamide and its pharmaceutically acceptable salts. US 4039672 . |
| 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) | 12416 | methyl 4-amino-2-methoxybenzoate | 27492-84-8 | C9H11NO3 | 详情 | 详情 |
| (II) | 32212 | methyl 4-amino-2-methoxy-5-nitrobenzoate | C9H10N2O5 | 详情 | 详情 | |
| (III) | 32213 | methyl 4,5-diamino-2-methoxybenzoate | C9H12N2O3 | 详情 | 详情 | |
| (IV) | 32214 | methyl 6-methoxy-1H-1,2,3-benzotriazole-5-carboxylate | C9H9N3O3 | 详情 | 详情 | |
| (V) | 32211 | (1-allyl-2-pyrrolidinyl)methanamine; (1-allyl-2-pyrrolidinyl)methylamine | 66411-51-6 | C8H16N2 | 详情 | 详情 |