tert-butyl 4-(2-bromoacetyl)-3-(3,4-dichlorophenyl)-1-piperazinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】47953

【品名】tert-butyl 4-(2-bromoacetyl)-3-(3,4-dichlorophenyl)-1-piperazinecarboxylate

【CA登记号】

【分子式】C₁₇H₂₁BrCl₂N₂O₃

【分子量】452.17482

【元素组成】C 45.16% H 4.68% Br 17.67% Cl 15.68% N 6.2% O 10.61%

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：(XV)

In a related method, the 2-arylpiperazine (IV) was first protected as the 4-tert-butyl carbamate (XIV) upon treatment with di-tert-butyl dicarbonate in MeOH at -78 C. Subsequent acylation of (XIV) with bromoacetyl bromide (XI) produced the bromo amide (XV), which was then condensed with the aminopiperidine (XIII), yielding the glycinamide derivative (XVI). Acidic cleavage of the Boc group of (XVI) afforded the 1-acyl piperazine (XVII). This was finally coupled with 3,5-dimethylbenzoic acid using EDC and HOBt.

参考文献中间体

合成目标

【1】 Anthes, J.C.; McPhail, A.T.; Blythin, D.J.; Shue, H.-J.; Chen, X.; Piwinski, J.J.; shih, N.-Y.; Discovery of Sch 62373 and analogs, of novel series of 2-phenylpiperazines exhibiting potent dual NK1/NK2 antagonist activity. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 244.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	47946	2-(3,4-dichlorophenyl)piperazine		C₁₀H₁₂Cl₂N₂	详情	详情
(IX)	26775	3,5-dimethylbenzoic acid	499-06-9	C₉H₁₀O₂	详情	详情
(XI)	14005	2-Bromoacetyl bromide; Bromoacetyl bromide	598-21-0	C₂H₂Br₂O	详情	详情
(XIII)	34808	1-Benzyl-4-piperidinylamine; 1-Benzyl-4-piperidinamine; 4-Amino-1-benzylpiperidine	50541-93-0	C₁₂H₁₈N₂	详情	详情
(XIV)	47952	tert-butyl 3-(3,4-dichlorophenyl)-1-piperazinecarboxylate		C₁₅H₂₀Cl₂N₂O₂	详情	详情
(XV)	47953	tert-butyl 4-(2-bromoacetyl)-3-(3,4-dichlorophenyl)-1-piperazinecarboxylate		C₁₇H₂₁BrCl₂N₂O₃	详情	详情
(XVI)	47954	tert-butyl 4-[2-[(1-benzyl-4-piperidinyl)amino]acetyl]-3-(3,4-dichlorophenyl)-1-piperazinecarboxylate		C₂₉H₃₈Cl₂N₄O₃	详情	详情
(XVII)	47955	2-[(1-benzyl-4-piperidinyl)amino]-1-[2-(3,4-dichlorophenyl)-1-piperazinyl]-1-ethanone		C₂₄H₃₀Cl₂N₄O	详情	详情

Extended Information