【结 构 式】 |
【分子编号】59265 【品名】N-methyl-4-phenyl-1-trityl-4-piperidinamine; N-methyl-N-(4-phenyl-1-trityl-4-piperidinyl)amine 【CA登记号】 |
【 分 子 式 】C31H32N2 【 分 子 量 】432.60856 【元素组成】C 86.07% H 7.46% N 6.48% |
合成路线1
该中间体在本合成路线中的序号:(VIII)N-Benzyl-4-hydroxy-4-phenylpiperidine (II) was prepared by addition of phenyllithium to N-benzyl-4-piperidone (I). Carbinol (II) was then converted to acetamide (III) by acid-catalyzed Ritter reaction with acetonitrile. Replacement of the acetamido for an N-Boc group in (III) was effected by acidic hydrolysis of amide (III) to give (IV), followed by treatment with di-tert-butyl dicarbonate. The resultant 1-benzyl-4-(Boc-amino)-4-phenylpiperidine (V) was subjected to catalytic hydrogenolysis in the presence of Pd/C, and the N-debenzylated piperidine (VI) was reprotected as the N-trityl derivative (VII) by treatment with triphenylmethyl chloride and triethylamine. Reduction of the N-Boc group of (VII) by LiAlH4, yielded the N-methyl amine (VIII). After acylation of (VIII) with acetyl chloride to acetamide (IX), its N-trityl group was cleaved by treatment with hot aqueous formic acid to produce the intermediate piperidine (X).
【1】 Bichon, D.; Van Broeck, D.; Proietto, V.; Gueule, P.; Emonds-Alt, X. (Sanofi-Synthélabo); Novel N-(3,4-dichlorophenyl-propyl)-piperidine derivs. as selective human NK3-receptor antagonists. EP 0673928; FR 2717477; FR 2717478; FR 2719311; JP 1996048669; US 5741910; US 5942523; US 6124316 . |
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) | 15720 | 1-benzyltetrahydro-4(1H)-pyridinone; 1-Benzyl-4-piperidone; N-Benzyl-4-piperidone; 1-(benzyl)-4-piperidinone; 1-benzylpiperidin-4-one; 1-(benzyl)piperidin-4-one | 3612-20-2 | C12H15NO | 详情 | 详情 |
(II) | 29470 | 1-benzyl-4-phenyl-4-piperidinol | C18H21NO | 详情 | 详情 | |
(III) | 54993 | N-(1-benzyl-4-phenyl-4-piperidinyl)acetamide | C20H24N2O | 详情 | 详情 | |
(IV) | 54994 | 1-benzyl-4-phenyl-4-piperidinylamine; 1-benzyl-4-phenyl-4-piperidinamine | C18H22N2 | 详情 | 详情 | |
(V) | 59263 | tert-butyl 1-benzyl-4-phenyl-4-piperidinylcarbamate | C23H30N2O2 | 详情 | 详情 | |
(VI) | 54998 | tert-butyl 4-phenyl-4-piperidinylcarbamate | C16H24N2O2 | 详情 | 详情 | |
(VII) | 59264 | tert-butyl 4-phenyl-1-trityl-4-piperidinylcarbamate | C35H38N2O2 | 详情 | 详情 | |
(VIII) | 59265 | N-methyl-4-phenyl-1-trityl-4-piperidinamine; N-methyl-N-(4-phenyl-1-trityl-4-piperidinyl)amine | C31H32N2 | 详情 | 详情 | |
(IX) | 59266 | N-methyl-N-(4-phenyl-1-trityl-4-piperidinyl)acetamide | C33H34N2O | 详情 | 详情 | |
(X) | 59267 | N-methyl-N-(4-phenyl-4-piperidinyl)acetamide | C14H20N2O | 详情 | 详情 |