N,N-diethyl-4-formylbenzamide -Drug Synthesis Database

【结构式】

【分子编号】45932

【品名】N,N-diethyl-4-formylbenzamide

【CA登记号】

【分子式】C₁₂H₁₅NO₂

【分子量】205.25664

【元素组成】C 70.22% H 7.37% N 6.82% O 15.59%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XII)

In a different synthetic strategy, 4-formylbenzoic acid (XI) was first coupled to diethylamine by means of EDC to yield N,N-diethyl 4-formylbenzamide (XII). The intermediate iminium salt produced by condensation between aldehyde (XII) and the chiral piperazine (IX) was then isolated as the benzotriazole adduct (XIII). Displacement of the benzotriazolyl group by the Grignard reagent (XIV) produced the title diastereoisomer as the major product, which was further enriched by recrystallization from acetonitrile/water.

参考文献中间体

合成目标

【1】 Report from ASCO 2002 - Docetaxel improves survival in node-positive early-stage breast cancer patients. Oncology (USA) 2002, 16, 8, 1054.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IX)	20690	(2R,5S)-1-allyl-2,5-dimethylpiperazine		C₉H₁₈N₂	详情	详情
(XI)	18922	4-formylbenzoic acid	619-66-9	C₈H₆O₃	详情	详情
(XII)	45932	N,N-diethyl-4-formylbenzamide		C₁₂H₁₅NO₂	详情	详情
(XIII)	56251	4-[[(2S,5R)-4-allyl-2,5-dimethylpiperazinyl](1H-1,2,3-benzotriazol-1-yl)methyl]-N,N-diethylbenzamide		C₂₇H₃₆N₆O	详情	详情
(XIV)	35984	bromo(3-methoxyphenyl)magnesium	36282-40-3	C₇H₇BrMgO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

8-Bromoquinoline (I) is treated with sec-BuLi in THF to afford lithium derivative (II), which then reacts with carbaldehyde (III) in THF to provide alcohol (IV). Finally, (IV) is converted into the desired compound by chlorination with SOCl2 in CH2Cl2 followed by reaction with piperazine (V) in refluxing acetonitrile.

参考文献中间体

合成目标

【1】 Delorme, D.; Wei, Z.-Y.; Plobeck, N.; et al.; New diarylmethylpiperazines as potent and selective nonpeptide delta opioid receptor agonists with increased in vitro metabolic stability. J Med Chem 2000, 43, 21, 3878.

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)	45930	8-bromoquinoline	16567-18-3	C₉H₆BrN	详情	详情
(II)	45931	8-quinolinyllithium		C₉H₆LiN	详情	详情
(III)	45932	N,N-diethyl-4-formylbenzamide		C₁₂H₁₅NO₂	详情	详情
(IV)	45933	N,N-diethyl-4-[hydroxy(8-quinolinyl)methyl]benzamide		C₂₁H₂₂N₂O₂	详情	详情
(V)	10355	Diethylenediamine; Piperazine	110-85-0	C₄H₁₀N₂	详情	详情

Extended Information