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【结 构 式】 
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【分子编号】54992 【品名】2-[(2R)-4-benzoyl-2-(3,4-difluorophenyl)morpholinyl]ethyl methanesulfonate 【CA登记号】 |
【 分 子 式 】C20H21F2NO5S 【 分 子 量 】425.4532864 【元素组成】C 56.46% H 4.98% F 8.93% N 3.29% O 18.8% S 7.54% |
合成路线1
该中间体在本合成路线中的序号：(XIV)Benzamide (XII) was prepared by acylation of morpholine (X) with benzoyl chloride (XI). The benzoate ester of (XII) was subsequently hydrolyzed under basic conditions to the alcohol (XIII), which was further converted to the mesylate ester (XIV) by means of methanesulfonyl chloride and triethylamine.
| 【1】 Emonds-Alt, X.; Grossriether, I.; Gueule, P.; Proietto, V.; Van Broeck, D. (Sanofi-Synthélabo); Substd. heterocyclic cpds., preparation method therefor and pharmaceutical compsns. containing same. EP 1156049; FR 2729952; FR 2729953; FR 2729954; JP 1999507324; JP 2001131171; US 5641777; WO 9623787 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 54989 | 2-[(2R)-2-(3,4-difluorophenyl)morpholinyl]ethyl benzoate | C19H19F2NO3 | 详情 | 详情 | |
| (XI) | 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 |
| (XII) | 54990 | 2-[(2R)-4-benzoyl-2-(3,4-difluorophenyl)morpholinyl]ethyl benzoate | C26H23F2NO4 | 详情 | 详情 | |
| (XIII) | 54991 | [(2R)-2-(3,4-difluorophenyl)-2-(2-hydroxyethyl)morpholinyl](phenyl)methanone | C19H19F2NO3 | 详情 | 详情 | |
| (XIV) | 54992 | 2-[(2R)-4-benzoyl-2-(3,4-difluorophenyl)morpholinyl]ethyl methanesulfonate | C20H21F2NO5S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XIV)Acetamide (XVI) was obtained by the Ritter reaction of 1-benzyl-4-phenyl-piperidin-4-ol (XV) with acetonitrile. Acidic hydrolysis of amide (XVI) provided the aminopiperidine (XVII), which was converted into urea (XVIII) upon treatment with N,N-dimethylcarbamoyl chloride. Hydrogenolytic cleavage of the N-benzyl group of (XVIII) gave piperidine (XIX), which was finally alkylated with the mesylate (XIV) to furnish the title compound.
| 【1】 Emonds-Alt, X.; Grossriether, I.; Gueule, P.; Proietto, V.; Van Broeck, D. (Sanofi-Synthélabo); Substd. heterocyclic cpds., preparation method therefor and pharmaceutical compsns. containing same. EP 1156049; FR 2729952; FR 2729953; FR 2729954; JP 1999507324; JP 2001131171; US 5641777; WO 9623787 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIV) | 54992 | 2-[(2R)-4-benzoyl-2-(3,4-difluorophenyl)morpholinyl]ethyl methanesulfonate | C20H21F2NO5S | 详情 | 详情 | |
| (XV) | 29470 | 1-benzyl-4-phenyl-4-piperidinol | C18H21NO | 详情 | 详情 | |
| (XVI) | 54993 | N-(1-benzyl-4-phenyl-4-piperidinyl)acetamide | C20H24N2O | 详情 | 详情 | |
| (XVII) | 54994 | 1-benzyl-4-phenyl-4-piperidinylamine; 1-benzyl-4-phenyl-4-piperidinamine | C18H22N2 | 详情 | 详情 | |
| (XVIII) | 54995 | N'-(1-benzyl-4-phenyl-4-piperidinyl)-N,N-dimethylurea | C21H27N3O | 详情 | 详情 | |
| (XIX) | 54996 | N,N-dimethyl-N'-(4-phenyl-4-piperidinyl)urea | C14H21N3O | 详情 | 详情 |