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【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information